Organic Reactions, Volume 88 E-Book
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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Serie: Organic Reactions
- Sprache: Englisch
Volume 88 represents the tenth single-chapter-volume produced in our 73-year history. Such single-chapter volumes represent definitive treatises on extremely important chemical transformations. The success of the research efforts over the past 20 years forms the basis for the single chapter in this volume namely, Hydroamination of Alkenes by Alexander L. Reznichenko and Kai C. Hultzsch. The authors have compiled an enormous (and growing) literature and distilled it into an extraordinarily useful treatise on all aspects of the hydroamination process.
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Veröffentlichungsjahr: 2016
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Table of Contents
Cover
Title Page
Copyright
Introduction to the Series Roger Adams, 1942
Introduction to the Series Scott E. Denmark, 2008
Preface to Volume 88
Chapter 1: Hydroamination of Alkenes
Acknowledgment
Introduction
Mechanism and Stereochemistry
Scope and Limitations
Applications to Synthesis
Comparison with Other Methods
Experimental Conditions
Experimental Procedures
Abbreviations Used in the Tabular Survey
References
Cumulative Chapter Titles by Volume
Author Index, Volumes 1-88
Chapter and Topic Index, Volumes 1-88
End User License Agreement
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Guide
Cover
Table of Contents
Introduction to the Series Roger Adams, 1942
Preface to Volume 88
Begin Reading
List of Illustrations
Chapter 1: Hydroamination of Alkenes
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
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Scheme 47
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Scheme 49
Scheme 50
Scheme 51
Scheme 52
Scheme 53
Scheme 54
Scheme 55
Scheme 56
Scheme 57
Scheme 58
Scheme 59
Scheme 60
Scheme 61
Scheme 62
Scheme 63
Scheme 64
Scheme 65
Scheme 66
Scheme 67
Scheme 68
Scheme 69
Scheme 70
Scheme 71
Scheme 72
Scheme 73
Scheme 74
Scheme 75
Scheme 76
Scheme 77
Scheme 78
Scheme 79
Scheme 80
Scheme 81
Scheme 82
Scheme 83
Scheme 84
Scheme 85
Scheme 86
Scheme 87
Scheme 88
Scheme 89
Scheme 90
Scheme 91
Scheme 92
Scheme 93
Scheme 94
Scheme 95
Scheme 96
Scheme 97
Scheme 98
Scheme 99
Scheme 100
Scheme 101
Scheme 102
Scheme 103
Scheme 104
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Scheme 107
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Scheme 109
Scheme 110
Scheme 111
Scheme 112
Scheme 113
Scheme 114
Scheme 115
Scheme 116
Scheme 117
Scheme 118
Scheme 119
Scheme 120
Scheme 121
Scheme 122
Scheme 123
Scheme 124
Scheme 125
Scheme 126
Scheme 127
Scheme 128
Scheme 129
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Scheme 131
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Scheme 134
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Scheme 136
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Scheme 138
Scheme 139
Scheme 140
Scheme 141
Scheme 142
Scheme 143
Scheme 144
Scheme 145
Scheme 146
Scheme 147
Scheme 148
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Scheme 156
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Scheme 168
Scheme 169
Scheme 170
Scheme 171
Scheme 172
Scheme 173
Scheme 174
Scheme 175
Scheme 176
Scheme 177
Figure 1 Stereomodels for observed diastereoselectivity in the cyclization of α-substituted aminopentene (left) and aminohexene (right) derivatives.
Advisory Board
John E. Baldwin
Peter Beak
Dale L. Boger
George A. Boswell, Jr.
André B. Charette
Engelbert Ciganek
Dennis Curran
Samuel Danishefsky
Huw M. L. Davies
John Fried
Jacquelyn Gervay-Hague
Heinz W. Gschwend
Stephen Hanessian
Richard F. Heck
Louis Hegedus
Robert C. Kelly
Andrew S. Kende
Laura Kiessling
Steven V. Ley
James A. Marshall
Michael J. Martinelli
Stuart W. McCombie
Jerrold Meinwald
Scott J. Miller
Larry E. Overman
Leo A. Paquette
Gary H. Posner
T. V. RajanBabu
Hans J. Reich
James H. Rigby
William R. Roush
Scott D. Rychnovsky
Martin Semmelhack
Charles Sih
Amos B. Smith, III
Barry M. Trost
Milán Uskokovic
James D. White
Peter Wipf
Former Members of the Board Now Deceased
Roger Adams
Homer Adkins
Werner E. Bachmann
A. H. Blatt
Robert Bittman
Virgil Boekelheide
Theodore L. Cairns
Arthur C. Cope
Donald J. Cram
David Y. Curtin
William G. Dauben
Louis F. Fieser
Ralph F. Hirshmann
Herbert O. House
John R. Johnson
Robert M. Joyce
Willy Leimgruber
Frank C. Mc Grew
Blaine C. Mc Kusick
Carl Niemann
Harold R. Snyder
Boris Weinstein
Organic Reactions
Volume 88
Editorial Board
Scott E. Denmark, Editor-in-Chief
Jeffrey Aubé
Jin K. Cha
André Charette
Vittorio Farina
Paul L. Feldman
Dennis G. Hall
Paul J. Hergenrother
Jeffrey S. Johnson
Marisa C. Kozlowski
Gary A. Molander
John Montgomery
Steven M. Weinreb
Robert M. Coates, Secretary University of Illinois at Urbana-Champaign, Urbana, Illinois
Jeffery B. Press, Secretary Press Consulting Partners, Brewster, New York
Linda S. Press, Editorial Coordinator
Danielle Soenen, Editorial Assistant
Dena Lindsay, Editorial Assistant
Engelbert Ciganek, Editorial Advisor
Associate Editors
Kai C. Hultzsch
Alexander L. Reznichenko
Copyright © 2016 by Organic Reactions, Inc. All rights reserved.
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Library of Congress Catalog Card Number: 42-20265
ISBN: 978-1-119-10385-1
Introduction to the Series Roger Adams, 1942
In the course of nearly every program of research in organic chemistry, the investigator finds it necessary to use several of the better-known synthetic reactions. To discover the optimum conditions for the application of even the most familiar one to a compound not previously subjected to the reaction often requires an extensive search of the literature; even then a series of experiments may be necessary. When the results of the investigation are published, the synthesis, which may have required months of work, is usually described without comment. The background of knowledge and experience gained in the literature search and experimentation is thus lost to those who subsequently have occasion to apply the general method. The student of preparative organic chemistry faces similar difficulties. The textbooks and laboratory manuals furnish numerous examples of the application of various syntheses, but only rarely do they convey an accurate conception of the scope and usefulness of the processes.
For many years American organic chemists have discussed these problems. The plan of compiling critical discussions of the more important reactions thus was evolved. The volumes of Organic Reactions are collections of chapters each devoted to a single reaction, or a definite phase of a reaction, of wide applicability. The authors have had experience with the processes surveyed. The subjects are presented from the preparative viewpoint, and particular attention is given to limitations, interfering influences, effects of structure, and the selection of experimental techniques. Each chapter includes several detailed procedures illustrating the significant modifications of the method. Most of these procedures have been found satisfactory by the author or one of the editors, but unlike those in Organic Syntheses, they have not been subjected to careful testing in two or more laboratories. Each chapter contains tables that include all the examples of the reaction under consideration that the author has been able to find. It is inevitable, however, that in the search of the literature some examples will be missed, especially when the reaction is used as one step in an extended synthesis. Nevertheless, the investigator will be able to use the tables and their accompanying bibliographies in place of most or all of the literature search so often required. Because of the systematic arrangement of the material in the chapters and the entries in the tables, users of the books will be able to find information desired by reference to the table of contents of the appropriate chapter. In the interest of economy, the entries in the indices have been kept to a minimum, and, in particular, the compounds listed in the tables are not repeated in the indices.
The success of this publication, which will appear periodically, depends upon the cooperation of organic chemists and their willingness to devote time and effort to the preparation of the chapters. They have manifested their interest already by the almost unanimous acceptance of invitations to contribute to the work. The editors will welcome their continued interest and their suggestions for improvements in Organic Reactions.
Introduction to the Series Scott E. Denmark, 2008
In the intervening years since “The Chief” wrote this introduction to the second of his publishing creations, much in the world of chemistry has changed. In particular, the last decade has witnessed a revolution in the generation, dissemination, and availability of the chemical literature with the advent of electronic publication and abstracting services. Although the exponential growth in the chemical literature was one of the motivations for the creation of Organic Reactions, Adams could never have anticipated the impact of electronic access to the literature. Yet, as often happens with visionary advances, the value of this critical resource is now even greater than at its inception.
From 1942 to the 1980's the challenge that Organic Reactions successfully addressed was the difficulty in compiling an authoritative summary of a preparatively useful organic reaction from the primary literature. Practitioners interested in executing such a reaction (or simply learning about the features, advantages, and limitations of this process) would have a valuable resource to guide their experimentation. As abstracting services, in particular Chemical Abstracts and later Beilstein, entered the electronic age, the challenge for the practitioner was no longer to locate all of the literature on the subject. However, Organic Reactions chapters are much more than a surfeit of primary references; they constitute a distillation of this avalanche of information into the knowledge needed to correctly implement a reaction. It is in this capacity, namely to provide focused, scholarly, and comprehensive overviews of a given transformation, that Organic Reactions takes on even greater significance for the practice of chemical experimentation in the 21st century.
Adams' description of the content of the intended chapters is still remarkably relevant today. The development of new chemical reactions over the past decades has greatly accelerated and has embraced more sophisticated reagents derived from elements representing all reaches of the Periodic Table. Accordingly, the successful implementation of these transformations requires more stringent adherence to important experimental details and conditions. The suitability of a given reaction for an unknown application is best judged from the informed vantage point provided by precedent and guidelines offered by a knowledgeable author.
As Adams clearly understood, the ultimate success of the enterprise depends on the willingness of organic chemists to devote their time and efforts to the preparation of chapters. The fact that, at the dawn of the 21st century, the series continues to thrive is fitting testimony to those chemists whose contributions serve as the foundation of this edifice. Chemists who are considering the preparation of a manuscript for submission to Organic Reactions are urged to contact the Editor-in-Chief.
Preface to Volume 88
The Prefaces to Volumes 78 and 85 highlighted the importance of nitrogen and nitrogen-containing compounds in the biosphere and the “chemosphere”. It is impossible to overstate the enormous diversity of organonitrogen substances as well as their critical role as agrochemicals, pharmaceuticals, and high-performance polymers. Nitrogen is so central to chemistry and life that it has also inspired writers and poets such as Sam Kean (The Disappearing Spoon) and Mario Markus (Chemical Poems: One for Each Element). However, no writer has matched the great Primo Levi in his ability to capture and express the personality and unique character of the elements as found in his classic compendium, The Periodic Table. In the chapter dedicated to Nitrogen, Levi observes:
“Nitrogen is nitrogen, it passes miraculously from the air into plants, from these into animals, and from animals to us; when its function in our body is exhausted, we eliminate it, but it still remains nitrogen, aseptic, innocent. We — I mean to say we mammals — who in general do have problems about obtaining water, have learned to wedge it into the urea molecule, which is soluble in water, and as urea we free ourselves of it; other animals, for whom water is precious, have made the ingenious invention of packaging their nitrogen in the form of uric acid, which is insoluble in water, and of eliminating it as a solid with no necessity of having recourse to water as a vehicle”.
Whereas the chapter that comprised Volume 85 concerned itself with the introduction of nitrogen into aromatic substances through the agency of copper-mediated cross-coupling reactions, the chapter in this volume focuses on the introduction of nitrogen into aliphatic substances, both cyclic and acyclic. Although many such methods have been in use for decades, such as nucleophilic displacement with amines, azides, and nitrites, the most atom-economical method involves the addition of an N–H bond across an unsaturated linkage (alkene, alkyne, allene, diene, etc.). This construct has been the subject of intense investigation only in the past two decades, with a staggering increase in the past ten years. Indeed, the ability to create organonitrogen compounds from alkenes and ammonia may become the modern day equivalent of the Haber-Bosch process which revolutionized agriculture (and unfortunately also warfare).
The success of the research efforts over the past 20 years forms the basis for the single chapter in this volume namely, Hydroamination of Alkenes by Alexander L. Reznichenko and Kai C. Hultzsch. The Board of Editors was hesitant to commission a chapter of this magnitude, but the importance of the chemistry motivated the search for authors with expertise and commitment to undertake such a massive effort. Our hopes could not have been better rewarded. The authors, Drs. Reznichenko and Hultzsch, have compiled an enormous (and growing) literature and distilled it into an extraordinarily useful treatise on all aspects of the hydroamination process. Given the myriad types of unsaturated substrates, metal-based catalysts, and reaction conditions, the authors have done an outstanding job of identifying the best options for various permutations of amine type and alkene structure. This comprehensive treatment of so many different options constitutes a dream “field guide” for the perplexed chemist who wants to know how best to approach the formation of a C-N bond in a target structure to form new stereogenic centers as well as rings of various sizes. Much of the focus in recent years has been on the development of chiral ligand sets for various metals to effect enantioselective hydroaminations. The authors have compiled the state of the art in this field in a scholarly, separate section.
The Tabular Survey is logically organized by substrate structure and further subdivided by inter- and intramolecular reactions as well as enantioselective reactions. This highly user-friendly structure assures the reader to be able to locate relevant precedent with ease. Given the magnitude of this undertaking, the authors had to establish the literature coverage at the outset of the project, January 2011. However, they have provided a supplemental reference list that includes all reports appearing between February 2011 and April 2015.
Volume 88 represents the tenth single-chapter-volume produced in our 73-year history. Such single-chapter volumes represent definitive treatises on extremely important chemical transformations. The organic chemistry community owes an enormous debt of gratitude to the authors of such chapters for the generous contribution of their time, effort, and insights on reactions that we clearly value.
It is appropriate here to acknowledge the expert assistance of the entire editorial board, in particular, André Charette who shepherded this massive chapter to completion. The contributions of the authors, editors, and the publisher were expertly coordinated by the responsible secretaries, Robert Coates and Jeffery Press. In addition, the Organic Reactions enterprise could not maintain the quality of production without the dedicated efforts of its editorial staff, Dr. Linda S. Press, Dr. Danielle Soenen, and Dr. Dena Lindsay. Insofar as the essence of Organic Reactions chapters resides in the massive tables of examples, the authors' and editorial coordinators' painstaking efforts are highly prized.
Scott E. DenmarkUrbana, Illinois
Chapter 1Hydroamination of Alkenes
Alexander L. Reznichenko
Borealis Polymers Oy, PO Box 330, 06101, Porvoo, Finland
Kai C. Hultzsch
University of Vienna, Faculty of Chemistry, Institute of Chemical Catalysis, Währinger Strasse 38, A-1090, Vienna, Austria
Contents
Acknowledgment
Introduction
Mechanism and Stereochemistry
Alkali, Alkaline Earth, and Rare Earth Metals
Group 4 and Group 5 Transition Metals
Late Transition Metals
Scope and Limitations
Ethylene and Other Unactivated Alkenes
Intermolecular Hydroamination of C
2
–C
4
Alkenes
Intermolecular Hydroamination of Unactivated Higher Alkenes
Intramolecular Hydroamination of Aminoalkenes
Hydroamination of Vinyl Arenes
Intermolecular Hydroamination of Vinyl Arenes
Intramolecular Hydroamination of Vinyl Arenes
Hydroamination of Conjugated Dienes
Intermolecular Hydroamination of 1,3-Dienes
Intramolecular Hydroamination of Aminodienes
Hydroamination of Allenes
Intermolecular Hydroamination of Allenes
Intramolecular Hydroamination of Aminoallenes
Hydroamination of Strained Alkenes
Hydroamination of Methylenecyclopropanes
Hydroamination of Norbornene
Intramolecular Hydroamination of Strained Alkenes
Enantioselective Hydroaminations
Enantioselective Intermolecular Hydroamination of Unactivated Alkenes
Enantioselective Intramolecular Hydroamination of Aminoalkenes
Enantioselective Intermolecular Hydroamination of Vinyl Arenes
Enantioselective Intramolecular Hydroamination Reactions of 1,3-Dienes
Enantioselective Intermolecular Hydroamination of 1,3-Dienes
Enantioselective Intramolecular Hydroamination of Aminodienes
Enantioselective Intramolecular Hydroamination of Aminoallenes
Enantioselective Hydroamination of Norbornene
Hydroamination/Carbocyclization
Applications to Synthesis
Comparison with Other Methods
Hydroelementation/Amination
Catalytic Hydroboration/Amination
Hydrozirconation/Iodination of Aminoalkenes
Cope-Type Hydroamination
Aminomercuration/Demercuration
Radical-Transfer Hydroamination
Experimental Conditions
Experimental Procedures
(
R
)-
N
-Benzylheptan-2-amine (Lanthanide-Catalyzed Asymmetric Intermolecular Hydroamination of an Aliphatic Terminal Alkene)
5-Methyl-10,11-dihydro-5
H
-dibenzo[
a
,
d
]cyclohepten-5,10-imine (MK-801) (Organolanthanide-Catalyzed Intramolecular Hydroamination of an Aminoalkene)
O
-Methylmetazocine (Lithium Amide-Catalyzed Intramolecular Hydroamination of an Aminoalkene)
(S)
-(+)-1-Phenylpent-4-enylamine (Kinetic Resolution of a Racemic Aminoalkene])
1-Phenyl-2,3-dihydroindole (Potassium-Catalyzed Addition of Aniline to 2-Chlorostyrene with Subsequent Cyclization)
(
S
)-
N
-Phenyl-
N
-[1-{4-(trifluoromethyl)phenyl}ethyl]amine (Palladium-Catalyzed Asymmetric Intermolecular Hydroamination of a Vinyl Arene)
1-Phenylmethyl-4-(2-phenethyl)piperazine (Lithium-Catalyzed Intermolecular Hydroamination of Styrene)
3-Fluoro-6,6,9-trimethyl-5,6-dihydrophenanthridine (Brønsted Acid-Catalyzed Intramolecular Hydroamination)
(
E
)-
N,N
-Diethyl-3,7-dimethyl-2,6-octadien-1-amine (
N,N
-Diethylgeranylamine) (Lithium-Catalyzed Addition of a Secondary Amine to a Diene)
8-Phenylmethyl-8-azabicyclo[3.2.1]oct-2-ene (Palladium-Catalyzed Intermolecular Transannular Hydroamination of a Cyclic Triene)
1-Benzyloxycarbonyl-2-[(
E
)-prop-1-enyl]piperidine (Organolanthanide-Catalyzed Intramolecular Hydroamination of an Aminodiene with Subsequent Protection)
(3
S
,5
R
,8
S
)-3-(1-Heptyl)-5-methylpyrrolizidine ((+)-Xenovenine) (Organolanthanide-Catalyzed Stereoselective Intramolecular Hydroamination of an Aminoallene)
2-(4-Fluorophenyl)-6-methyl-2,3,4,5-tetrahydropyridine (Group 4 Metal-Catalyzed Intramolecular Hydroamination of an Aminoallene)
2-(Cyclohexylidenemethyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine (Gold-Catalyzed Asymmetric Intramolecular Hydroamination of a Protected Aminoallene)
2-Methyl-2,3,5,9b-tetrahydro-1
H
-pyrrolo[2,1-
a
]isoindole (Lanthanide-Catalyzed Sequential Hydroamination/Carbocyclization)
Abbreviations Used in the Tabular Survey
Chart 1. Catalysts and Ligands Used in the Tables
Table 1A. Hydroamination of Simple Alkenes
Table 1B. Hydroamination of Vinyl Arenes
Table 1C. Hydroamination of 1,3-Dienes
Table 1D. Hydroamination of Allenes
Table 1E. Hydroamination of Strained Alkenes
Table 2A. Hydroamination/Cyclization of Aminoalkenes
Table 2B. Hydroamination/Cyclization of Vinyl Arenes
Table 2C. Hydroamination/Cyclization of Aminodienes
Table 2D. Hydroamination/Cyclization of Aminoallenes
Table 2E. Hydroamination/Cyclization of Strained Aminoalkenes
Table 3A. Enantioselective Hydroamination of Simple Alkenes
Table 3B. Enantioselective Hydroamination of Vinyl Arenes
Table 3C. Enantioselective Hydroamination of 1,3-Dienes
Table 3D. Enantioselective Hydroamination of Allenes
Table 3E. Enantioselective Hydroamination of Strained Alkenes
Table 4A. Enantioselective Hydroamination/Cyclization of Aminoalkenes
Table 4B. Enantioselective Intramolecular Hydroamination of Vinyl Arenes
Table 4C. Enantioselective Hydroamination/Cyclization of Aminodienes
Table 4D. Enantioselective Hydroamination/Cyclization of Aminoallenes
Table 5. Hydroamination/Carbocyclization of Aminoalkenes
References
Acknowledgment
Generous financial support by the National Science Foundation through a NSF CAREER Award (CHE 0956021) and the ACS Petroleum Research Fund (PRF #49109-ND1) is gratefully acknowledged.
Introduction*
The development of efficient synthetic procedures for establishing carbon–nitrogen bonds has received significant attention over the last one and a half centuries, due to the importance of nitrogen-containing compounds in biological systems and pharmaceutical applications.1, 2
