Science of Synthesis Knowledge Updates 2010 Vol. 1 E-Book

• Herausgeber: Thieme
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 1003

Veröffentlichungsjahr: 2014

Beschreibung

The Science of Synthesis Editorial Board,together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Four annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.

Content of this volume:
Germanium cyanides, acylgermanes, a-halo- and a-alkoxyvinylgermanes, a-halo-, a-hydroxy-, a-alkoxy-, and a-aminoalkylgermanes, alkynylgermanes, aryl- and heteroarylgermanes, propargyl- and allenylgermanes, selenophenes,
tellurophenes, isoxazoles, 1,2-benzisoxazoles and related compounds, benzoxazoles and other annulated oxazoles, isothiazoles, benzisothiazoles, benzothiazoles, isoselenazoles, annulated isoselenazole compounds, selenazoles, annulated selenazole compounds, isotellurazoles, and annulated isotellurazole and tellurazole compounds, pyridopyrazines and iodoarenes.

Leseprobe

Science of Synthesis

Science of Synthesis is the authoritative and comprehensive reference work for the entire field of organic and organometallic synthesis.

Science of Synthesis presents the important synthetic methods for all classes of compounds and includes:

Methods critically evaluated by leading scientists

Background information and detailed experimental procedures

Schemes and tables which illustrate the reaction scope

Preface

As the pace and breadth of research intensifies, organic synthesis is playing an increasingly central role in the discovery process within all imaginable areas of science: from pharmaceuticals, agrochemicals, and materials science to areas of biology and physics, the most impactful investigations are becoming more and more molecular. As an enabling science, synthetic organic chemistry is uniquely poised to provide access to compounds with exciting and valuable new properties. Organic molecules of extreme complexity can, given expert knowledge, be prepared with exquisite efficiency and selectivity, allowing virtually any phenomenon to be probed at levels never before imagined. With ready access to materials of remarkable structural diversity, critical studies can be conducted that reveal the intimate workings of chemical, biological, or physical processes with stunning detail.

The sheer variety of chemical structural space required for these investigations and the design elements necessary to assemble molecular targets of increasing intricacy place extraordinary demands on the individual synthetic methods used. They must be robust and provide reliably high yields on both small and large scales, have broad applicability, and exhibit high selectivity. Increasingly, synthetic approaches to organic molecules must take into account environmental sustainability. Thus, atom economy and the overall environmental impact of the transformations are taking on increased importance.

The need to provide a dependable source of information on evaluated synthetic methods in organic chemistry embracing these characteristics was first acknowledged over 100 years ago, when the highly regarded reference source Houben–Weyl Methoden der Organischen Chemie was first introduced. Recognizing the necessity to provide a modernized, comprehensive, and critical assessment of synthetic organic chemistry, in 2000 Thieme launched Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. This effort, assembled by almost 1000 leading experts from both industry and academia, provides a balanced and critical analysis of the entire literature from the early 1800s until the year of publication. The accompanying online version of Science of Synthesis provides text, structure, substructure, and reaction searching capabilities by a powerful, yet easy-to-use, intuitive interface.

From 2010 onward, Science of Synthesis is being updated quarterly with high-quality content via Science of Synthesis Knowledge Updates. The goal of the Science of Synthesis Knowledge Updates is to provide a continuous review of the field of synthetic organic chemistry, with an eye toward evaluating and analyzing significant new developments in synthetic methods. A list of stringent criteria for inclusion of each synthetic transformation ensures that only the best and most reliable synthetic methods are incorporated. These efforts guarantee that Science of Synthesis will continue to be the most up-to-date electronic database available for the documentation of validated synthetic methods.

Also from 2010, Science of Synthesis includes the Science of Synthesis Reference Library, comprising volumes covering special topics of organic chemistry in a modular fashion, with six main classifications: (1) Classical, (2) Advances, (3) Transformations, (4) Applications, (5) Structures, and (6) Techniques. Titles will include Stereoselective Synthesis, Water in Organic Synthesis, and Asymmetric Organocatalysis, among others. With expertevaluated content focusing on subjects of particular current interest, the Science of Synthesis Reference Library complements the Science of Synthesis Knowledge Updates, to make Science of Synthesis the complete information source for the modern synthetic chemist.

The overarching goal of the Science of Synthesis Editorial Board is to make the suite of Science of Synthesis resources the first and foremost focal point for critically evaluated information on chemical transformations for those individuals involved in the design and construction of organic molecules.

Throughout the years, the chemical community has benefited tremendously from the outstanding contribution of hundreds of highly dedicated expert authors who have devoted their energies and intellectual capital to these projects. We thank all of these individuals for the heroic efforts they have made throughout the entire publication process to make Science of Synthesis a reference work of the highest integrity and quality.

The Editorial Board

July 2010

E. M. Carreira (Zurich, Switzerland)

C. P. Decicco (Princeton, USA)

A. Fuerstner (Muelheim, Germany)

G. A. Molander (Philadelphia, USA)

P. J. Reider (Princeton, USA)

E. Schaumann (Clausthal-Zellerfeld, Germany)

M. Shibasaki (Tokyo, Japan)

E. J. Thomas (Manchester, UK)

B. M. Trost (Stanford, USA)

Abstracts

5.1.1.8 Germanium Hydrides

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of germanium hydrides, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · hydrides · germyl hydride · germanium hydride · radical reduction · hydrogermylation · germylation · tris(2-furyl)germane · cross coupling · germyl cation

5.1.15.2 Germanium Cyanides

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of germanium cyanides, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · cyanides · cyanation · halides · silver · germole

5.1.16.6 Acylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of acylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · enol ethers · [2+2] cycloaddition · azetidines · BINAP · alkynes · carbonylation · furans · radicals · polymerization · amides

5.1.18.4 α-Halo- and α-Alkoxyvinylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of α-halo- and α-alkoxyvinylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · substitution · hydrometalation · carbometalation · halogenation · alkynes · germatranes · desulfonylation · cross coupling · palladium(0) · styrenes

5.1.19.7 α-Halo-, α-Hydroxy,- α-Alkoxy-, and α-Aminoalkylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of α-halo-, α-hydroxy-, α-alkoxy-, and α-aminoalkylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · [1,2] rearrangements · oxo-carbenium · oxonium · substitution · hydroboration · boronic ester · [3+2] cycloaddition · germenes · silylation · borylation

5.1.20.4 Alkynylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkynylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · alkynes · [3+2] cycloadditions · hydrostannylation · hydroboration · cross coupling · palladium(0) · substitution · cross metathesis · elimination · Pauson–Khand reaction · cyclopentenones

5.1.22.6 Aryl- and Heteroarylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of aryl- and heteroarylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · cross coupling · Stille reaction · Hiyama–Denmark reaction · substitution · Barbier conditions · transmetalation · cycloaddition · solid-phase synthesis · traceless linkers

5.1.23.6 Vinylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of vinylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · vinylgermanes · alkenylgermanes · β-effect · hyperconjugation · hydrogermylation · heterogermylation · metallogermylation · cross coupling · germatranes

5.1.24.4 Propargyl- and Allenylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of propargyl- and allenylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · propargylgermanes · allenylgermanes · transmetalation · Grignard reagents · [2+2] cycloaddition

5.1.25.3 Benzylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of benzylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · benzylgermanes · cross coupling · boscalid

5.1.26.6 Allylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of allylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · alkenylgermanes · allylation · germylene · π-allylpalladium(0) · metallogermanes · Baylis–Hillman · germyl radicals

5.1.27.4 Alkylgermanes

A. C. Spivey and C.-C. Tseng

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkylgermanes, their properties, and synthetic reactions. It focuses on the literature published in the period 2001–2009.

Keywords: germanes · germanium compounds · alkenylgermanes · ADMET · germylene · hydrogermylation

9.11.4 Selenophenes

J. Schatz and M. Seßler

This manuscript is intended to update the first report on the synthesis of selenophenes in Science of Synthesis and will briefly summarize essential, more recent findings concerning this heterocyclic system in the first decade of the new millennium. During this time, applications of selenophene-based materials in organic electronics and photonics received considerable interest, and selenophene-containing π-conjugated compounds have been proposed as organic magnetic materials.

Keywords: selenophenes · active methylene compounds · selanylenynes · cyclization · aromatization · metal–halogen exchange

9.12.3 Tellurophenes

J. Schatz and M. Seßler

This manuscript is intended to update the earlier report on the synthesis of tellurophenes in Science of Synthesis, and summarizes essential, more recent findings concerning this heterocyclic system in the first decade of the new millennium. The decade 2000–2010 saw an increasing interest in organic molecules as functional materials, shifting the focus away from biological or pharmaceutical application. This trend could especially be observed for thiophenes, leading, not surprisingly, also to an increasing pursuit of potential applications of tellurophenes.

Keywords: tellurophenes · tellanylenynes · cyclization · aryl cross coupling

11.9.5 Isoxazoles

P. Margaretha

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of isoxazoles (1,2-oxazoles). It focuses on the literature published in the period 2001–2009.

Keywords: isoxazoles · isoxazol-5-ones · dipolar cycloadditions · oximes · nitrile oxides · cyclization · multicomponent coupling · regioselectivity

11.10.5 1,2-Benzisoxazoles and Related Compounds

S. Härtinger

This update deals with important general methods for the synthesis of 1,2-benzisoxazole derivatives that have not been discussed in the original ▶ Section 11.10 or in Houben–Weyl, Vol. E 8a. Literature published until 2009 is reviewed.

Keywords: 1,2-benzisoxazoles · cyclization · ring closure · coupling reactions · aromatization

11.13 Product Class 13: Benzoxazoles and Other Annulated Oxazoles

M. Schnürch, J. Hämmerle, and P. Stanetty

This manuscript is a revision of the earlier Science of Synthesis contribution describing methods for the synthesis of benzoxazoles (benzo[d]oxazoles, 1,3-benzoxazoles) and related compounds such as benzoxazol-2-ones and other heteroannulated derivatives. Classical routes to benzoxazoles involve the intermolecular cyclization of 2-aminophenols or intramolecular cyclization of N-phenylcarboxamides, but more recent developments with different approaches are included as well.

Keywords: benzoxazoles · benzoxazol-2-ones · 2-aminophenols · N-phenylcarboxamides · cyclization · annulation · Beckmann rearrangement

11.15.4 Isothiazoles

M. Sainsbury

This manuscript is an update to the earlier Science of Synthesis contribution describing the syntheses of isothiazoles and, in particular, advances in classical methods. Applications of well-known coupling methods to isothiazoles are also illustrated. The coverage focuses on the literature published in the period 2001–2009.

Keywords: isothiazoles · isothiazol-3(2H)-ones · dipolar cycloadditions · nitrile sulfides · macrocycles · cyclization · coupling reactions · rearrangements

11.16.3 Benzisothiazoles

M. Sainsbury

This manuscript is an update of the earlier Science of Synthesis contribution describing methods for the syntheses of 1,2-benzisothiazoles (benzo[d]isothiazoles) and related compounds such as 2,1-benzisothiazoles (benzo[c]isothiazoles) and other heteroannulated derivatives, including 2-arylisothiazolo[5,4-b]pyridin-3(2H)-ones. New routes to 1,2-benzisothiazoles involve the intermolecular cyclizations of benzyne (generated in situ) with nitriles sulfides. Developments in approaches to 1,2-benzisothiazol-3(2H)ones are also described.

Keywords: 1,2-benzisothiazoles · 2,1-benzisothiazoles · saccharin · 1,3-dipolar addition · cyclization · cycloaddition · annulation · Suzuki coupling

11.17.6 Thiazoles

P. A. Koutentis and H. A. Ioannidou

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of aromatic thiazoles and the tautomers of heterosubstituted thiazoles. It focuses on the literature published in the period 1999–2009.

Keywords: thiazoles · ring closure · aromatization · ring transformation · substituent modification

11.18.5 Benzothiazoles

H. Ulrich

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of benzothiazoles. Recent interest in this area has in part been generated by the discovery that some 2-(aminophenyl)benzothiazoles, in particular, possess potent anticancer and other biological activities.

Keywords: benzothiazoles · 2-aminobenzenethiols · N-phenylthioamides · oxidative cyclization · solid-phase synthesis

11.20.3 Isoselenazoles

K. Shimada

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of isoselenazoles. It focuses on the literature published in the period 2002–2009.

Keywords: isoselenazoles · 4,5-diarylisoselenazoles · 3-(trihalomethyl)isoselenazoles · isoselenazole-3-carboxylic acids · 3,5-disubstituted isoselenazoles · bis(N,N-dimethylcarbamoyl) diselenide · ring closure · cyclization · substituent modification

11.21.5 Annulated Isoselenazole Compounds

K. Shimada

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of annulated isoselenazole compounds. It focuses on the literature published in the period 2002–2009.

Keywords: 1,2-benzisoselenazoles · 1,2-benzisoselenazol-3(2H)-ones · N,N′-dialkylisophthalamides · ring closure · ortho-metalation · selenation · oxidation

11.22.4 Selenazoles

K. Shimada

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of selenazoles. The synthesis of selenazoles by ring construction using selenocarbonyl compounds, such as selenoamides and selenoureas, is reported.

Keywords: selenazoles · ring closure · substituent modification · side-chain modification · dithioimidocarbonates · selenoamides · selenoureas · α-halo ketones · α-halo acetonitriles · selenazadienes · benzylic oxidation

11.23.3 Annulated Selenazole Compounds

K. Shimada

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of annulated selenazole compounds. It focuses on the literature published in the period 2002–2009.

Keywords: benzoselenazoles · 2-halophenyl isocyanides · annulation · ring closure · substrate modification · [1,3]selenazolo[4,5-d]triazines · selenazole-5-carbonitriles · benzoselenazol-3-ium salts · benzoselenazole-1,7-diones · squarylium dyes · azo dyes

11.25.4 Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds

K. Shimada

This manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of isotellurazoles, and annulated isotellurazole and tellurazole compounds. It focuses on the literature published in the period 2002–2009. An efficient, one-pot procedure for the preparation of 3,5-disubstituted isotellurazoles from alkynones and bis(N,N-dimethylcarbamoyl) ditelluride is reported.

Keywords: isotellurazoles · isotellurazole Te-oxides · benzotellurazoles · cyclization · ring closure · deoxygenation · ortho-metalation · telluration · oxidation

16.20.3 Pyridopyrazines

J. Zhang

This manuscript is an update of the original Science of Synthesis chapter and includes methods for the preparation of pyrido[2,3-b]pyrazines and pyrido[3,4-b]pyrazines described in the literature up to 2010. Methods proceeding via condensation of pyridinediamines with carbonyl compounds and the application of halopyrido[2,3-b]pyrazines in palladium-catalyzed cross-coupling reactions are covered.

Keywords: pyridopyrazines · ring closure · condensation reactions · dicarbonyl compounds · cross-coupling reactions · pyridinediamines

31.4.2.2 Iodoarenes

S. R. Waldvogel

This manuscript is an update of the 2007 Science of Synthesis contribution describing methods for the synthesis of iodoarenes published in the period 2006–2010.

Keywords: iodination · iodine · iodo compounds · phenols · napthoquinones · benzoquinones · halodecarboxylation · fluorine compounds · electrophilic aromatic substitution · aryl compounds · halogenation · activation of C–-H bonds · acid halides

Science of Synthesis Knowledge Updates 2010/1

Preface

Abstracts

Table of Contents

5.1.1.8 Germanium Hydrides (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.15.2 Germanium Cyanides (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.16.6 Acylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.18.4 α-Halo- and α-Alkoxyvinylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.19.7 α-Halo-, α-Hydroxy,- α-Alkoxy-, and α-Aminoalkylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.20.4 Alkynylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.22.6 Aryl- and Heteroarylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.23.6 Vinylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.24.4 Propargyl- and Allenylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.25.3 Benzylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.26.6 Allylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

5.1.27.4 Alkylgermanes (Update 2010)

A. C. Spivey and C.-C. Tseng

9.11.4 Selenophenes (Update 2010)

J. Schatz and M. Seßler

9.12.3 Tellurophenes (Update 2010)

J. Schatz and M. Seßler

11.9.5 Isoxazoles (Update 2010)

P. Margaretha

11.10.5 1,2-Benzisoxazoles and Related Compounds (Update 2010)

S. Härtinger

11.13 Product Class 13: Benzoxazoles and Other Annulated Oxazoles

M. Schnürch, J. Hämmerle, and P. Stanetty

11.15.4 Isothiazoles (Update 2010)

M. Sainsbury

11.16.3 Benzisothiazoles (Update 2010)

M. Sainsbury

11.17.6 Thiazoles (Update 2010)

P. A. Koutentis and H. A. Ioannidou

11.18.5 Benzothiazoles (Update 2010)

H. Ulrich

11.20.3 Isoselenazoles (Update 2010)

K. Shimada

11.21.5 Annulated Isoselenazole Compounds (Update 2010)

K. Shimada

11.22.4 Selenazoles (Update 2010)

K. Shimada

11.23.3 Annulated Selenazole Compounds (Update 2010)

K. Shimada

11.25.4 Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds (Update 2010)

K. Shimada

16.20.3 Pyridopyrazines (Update 2010)

J. Zhang

31.4.2.2 Iodoarenes (Update 2010)

S. R. Waldvogel

Author Index

Abbreviations

Table of Contents

Volume 5: Compounds of Group 14 (Ge, Sn, Pb)

5.1 Product Class 1: Germanium Compounds

5.1.1.8 Germanium Hydrides

A. C. Spivey and C.-C. Tseng

5.1.1.8 Germanium Hydrides

5.1.1.8.1 Method 1: Synthesis by Reduction of Germanium Halides

5.1.1.8.2 Method 2: Applications in Reduction of Organic Halides

5.1.1.8.3 Method 3: Applications in Hydrogermylation of C—C Multiple Bonds

5.1.1.8.4 Method 4: Applications with Acids and Bases

5.1.1.8.5 Method 5: Applications in Palladium(0)-Catalyzed Coupling Reactions

5.1.1.8.6 Method 6: Application as an Alternative to Tributyltin Hydride in Radical Chain Reactions

5.1.1.8.7 Method 7: Application as Precursors for Germyl Cation Generation

5.1.15.2 Germanium Cyanides

A. C. Spivey and C.-C. Tseng

5.1.15.2 Germanium Cyanides

5.1.15.2.1 Method 1: Synthesis from Halogermanes by Substitution with Trialkylsilyl Cyanides

5.1.16.6 Acylgermanes

A. C. Spivey and C.-C. Tseng

5.1.16.6 Acylgermanes

5.1.16.6.1 Method 1: Synthesis from Germyl Enol Ethers by Hydrolysis

5.1.16.6.2 Method 2: Synthesis from α,α-Diheterosubstituted Germanes by Hydrolysis

5.1.16.6.3 Method 3: Synthesis from Terminal Alkynes by Carbonylation

5.1.16.6.4 Method 4: Application of Acylgermanes as Radical Acceptors

5.1.16.6.5 Method 5: Application of Acylgermanes as Amide Precursors

5.1.18.4 α-Halo- and α-Alkoxyvinylgermanes

A. C. Spivey and C.-C. Tseng

5.1.18.4 α-Halo- and α-Alkoxyvinylgermanes

5.1.18.4.1 Method 1: Synthesis of α-Alkoxyvinylgermanes from α-Metallovinyl Ethers by Substitution

5.1.18.4.2 Method 2: Synthesis of α-Halovinylgermanes from Alk-1-ynylgermanes by Hydro/Carbometalation–Halogenation

5.1.18.4.3 Method 3: Synthesis of α-Halovinylgermanes from α-Halovinyl Sulfones by Radical-Mediated Desulfonylation

5.1.18.4.4 Method 4: Application of α-Halovinylgermanes in Palladium-Catalyzed Cross Coupling with Organic Halides

5.1.19.7 α-Halo-, α-Hydroxy,- α-Alkoxy-, and α-Aminoalkylgermanes

A. C. Spivey and C.-C. Tseng

5.1.19.7 α-Halo-, α-Hydroxy,- α-Alkoxy-, and α-Aminoalkylgermanes

5.1.19.7.1 Method 1: Synthesis of α-Hetero- and α-Haloalkylgermanes from Halogermanes by Substitution

5.1.19.7.2 Method 2: Synthesis by Interconversion of α-Hetero- and α-Haloalkylgermanes by Substitution

5.1.19.7.3 Method 3: Synthesis of α-Hydroxylalkylgermanes from Hydroboration of Vinylgermanes

5.1.19.7.4 Method 4: Synthesis of α-Aminoalkylgermanes by [3 + 2] Cycloaddition of Germenes to Imino Esters

5.1.19.7.5 Method 5: Application of Lithiated α-Haloalkylgermanes in gem-Silylation/Borylation Reactions To Give Polymetalated Methanes

5.1.20.4 Alkynylgermanes

A. C. Spivey and C.-C. Tseng

5.1.20.4 Alkynylgermanes

5.1.20.4.1 Method 1: Synthesis from Halogermanes by Substitution

5.1.20.4.2 Method 2: Synthesis from Group 14 Metalloalkynyls by Metathesis with Alkenylgermanes

5.1.20.4.3 Method 3: Synthesis by Substitution with Aminogermanes

5.1.20.4.4 Method 4: Synthesis by Elimination of α-Alkoxyalkenylgermanes

5.1.20.4.5 Method 5: Applications of Alkynylgermanes as Protecting Groups

5.1.20.4.6 Method 6: Applications of Alkynylgermanes in Palladium(0)-Catalyzed Cross-Coupling Reactions

5.1.22.6 Aryl- and Heteroarylgermanes

A. C. Spivey and C.-C. Tseng

5.1.22.6 Aryl- and Heteroarylgermanes

5.1.22.6.1 Method 1: Synthesis from Halogermanes by Substitution with Arylmetals

5.1.22.6.1.1 Variation 1: Using Preformed Arylmetals

5.1.22.6.1.2 Variation 2: Using Barbier-Type Reactions

5.1.22.6.2 Method 2: Synthesis from Aryl Halides by Palladium(0)-Mediated Coupling with Germanium Hydrides

5.1.22.6.3 Method 3: Synthesis from Arylstannanes by Transmetalation with Germanium(IV) Chloride

5.1.22.6.4 Method 4: Synthesis of Aryl- and Heteroarylgermanes by Cycloaddition

5.1.22.6.5 Method 5: Applications of Arylgermanes as Linkers for Solid-Phase Synthesis

5.1.22.6.6 Method 6: Applications of Arylgermanes in Palladium(0)-Catalyzed Cross-Coupling Reactions

5.1.23.6 Vinylgermanes

A. C. Spivey and C.-C. Tseng

5.1.23.6 Vinylgermanes

5.1.23.6.1 Method 1: Synthesis from Vinyllithium and Vinyl Grignard Reagents by Transmetalation with Halogermanes

5.1.23.6.2 Method 2: Synthesis from Alkynes by Hydro-, Hetero-, and Metallogermylation

5.1.23.6.2.1 Variation 1: By Hydrogermylation

5.1.23.6.2.2 Variation 2: By Palladium(0)-Mediated Germylation

5.1.23.6.2.3 Variation 3: By Metallogermylation

5.1.23.6.3 Method 3: Synthesis from Vinylgermanes by Ruthenium-Catalyzed Metathesis

5.1.23.6.4 Method 4: Applications in Palladium(0)-Catalyzed Cross Coupling of-Organic Halides

5.1.24.4 Propargyl- and Allenylgermanes

A. C. Spivey and C.-C. Tseng

5.1.24.4 Propargyl- and Allenylgermanes

5.1.24.4.1 Method 1: Synthesis of Propargyl- and Allenylgermanes by Substitution

5.1.24.4.2 Method 2: Application of Allenylgermanes in [2 + 2]-Cycloaddition Reactions with Imino Esters