Applied Cross-Coupling Reactions

245 Pages·2013·18.891 MB·English

by  Yaushi Nishihara (auth.), Yasushi Nishihara (eds.)

Lecture Notes in Chemistry
Volume 80
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Yasushi Nishihara
Editor
Applied Cross-Coupling
Reactions
123
Editor
Yasushi Nishihara
Department of Chemistry
Okayama University
Okayama
Japan
ISSN 0342-4901 ISSN 2192-6603 (electronic)
ISBN 978-3-642-32367-6 ISBN 978-3-642-32368-3 (eBook)
DOI 10.1007/978-3-642-32368-3
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Preface
The cross-coupling reactions, developed for the first time in the 1970s, were
acknowledgedbytheawardoftheNobelPrizeinChemistrytothreeresearchersin
December,2010.Thesecross-couplingreactionshavebeendevelopedremarkably
over the past 40 years vis-à-vis a variety of transition metal catalysts, organome-
tallic reagents, and organic halides. They have enabled the formation of carbon–
carbon bonds between unsaturated organic compounds, which is the fundamental
framework of organic synthesis. It has become possible to produce extremely
complex molecules through the development of the cross-coupling reactions, and
asaresult,highlyselectivecarbon–carbon-bondingreactionshavebeenachieved.
The large number of publications concerning cross-coupling is continually
increasing.Thekindsoftransitionmetalsusedascatalysts,andtheorganometallic
reagents used as coupling partners have also widely expanded in recent years.
It has become possible to form a variety of very specific types of carbon–carbon
bonds through appropriate selection of the reagents.
Althoughtherearenumerousbooksandreviewsonthecross-couplingreactions,
until now most of these books have been mainly categorized according to the
eponymous(named)reactions.Thecross-couplingreactionshavehadatremendous
impactnotonlyinacademicarenasbutalsoinindustry.Thesecatalyzedreactions
areaccomplishedusingthetransitionmetalcomplexeswithextremelyhighutility.
In this book, from the viewpoint of application, the authors select several repre-
sentative cross-coupling reactions and classify the types of compounds using the
mostup-to-datereferencesavailable.Theauthorsrefertothehistoricalbackground
ofthecross-couplingreactionsandtothereactionmechanisms.Thenthecategories
of compounds are outlined in order of natural products, pharmaceuticals, liquid
crystals,andconjugatepolymers.Finally,recentprogressisintroducedintheform
of the new cross-coupling reactions involving aryl chlorides and alkyl halides
bearingb-hydrogenascouplingelectrophiles.
The authors hope that this book will provide the fundamental basics to both
undergraduate and graduate-student readers, but also wish to inspire continued
development and innovation of the cross-coupling reactions.
v
vi Preface
Finally,thanksgoesouttoDr.RoderickO’Brienforhishelpfulinputduringthe
preparationofthismanuscriptandtotheeditorialteamatSpringerDE,inparticular,
ElizabethHawkinsandBeateSiekfortheirpatienceandguidanceduringtheentire
projects.
Okayama, Japan, 2012 Yasushi Nishihara
Contents
Part I Metal-Catalyzed Cross-Coupling Reactions
1 A Historic Overview of the Metal-Catalyzed
Cross-Coupling Reactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.1 General Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.2 The Cross-Coupling Reactions Addressed in this Textbook . . . . 5
1.2.1 Kumada–Tamao–Corriu Coupling. . . . . . . . . . . . . . . . . 5
1.2.2 Murahashi Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . 6
1.2.3 Sonogashira–Hagihara Coupling. . . . . . . . . . . . . . . . . . 7
1.2.4 Negishi Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
1.2.5 Migita–Kosugi–Stille Coupling. . . . . . . . . . . . . . . . . . . 8
1.2.6 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . 8
1.2.7 Hiyama Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
1.3 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
2 Mechanisms and Fundamental Reactions . . . . . . . . . . . . . . . . . . . 17
2.1 Transmetalation in Suzuki–Miyaura Coupling. . . . . . . . . . . . . . 17
2.1.1 Stoichiometric Reactions of Suzuki–Miyaura
Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19
2.1.2 Base-Assisted Transmetalation . . . . . . . . . . . . . . . . . . . 20
2.1.3 The Turnover Limiting Step in Suzuki–Miyaura
Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
2.1.4 Pathways for Transmetalation. . . . . . . . . . . . . . . . . . . . 23
2.1.5 Computational Studies of the Transmetalation
Step in Suzuki–Miyaura Coupling. . . . . . . . . . . . . . . . . 25
2.1.6 An Interconversion Between Trifluoroborate
and Boronic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28
vii
viii Contents
2.2 The ‘‘Copper Effect’’ in Migita–Kosugi–Stille Coupling. . . . . . . 30
2.2.1 A Cine Substitution Reaction. . . . . . . . . . . . . . . . . . . . 30
2.2.2 The Copper Effect. . . . . . . . . . . . . . . . . . . . . . . . . . . . 32
2.2.3 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34
2.3 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
Part II Applications of the Cross-Coupling Reactions
3 Natural Product Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
3.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
3.2 Kumada–Tamao–Corriu Coupling (sp3–sp2) . . . . . . . . . . . . . . . 44
3.3 Sonogashira–Hagihara Coupling (sp–sp2). . . . . . . . . . . . . . . . . 46
3.4 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
3.4.1 sp2–sp2 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . 49
3.4.2 sp3–sp2 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . 50
3.4.3 sp–sp2 Negishi Coupling . . . . . . . . . . . . . . . . . . . . . . . 52
3.4.4 Carbometalation and Negishi Coupling Sequences . . . . . 52
3.4.5 Utility of Negishi Coupling toward Carbonyl
Compound Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . 54
3.5 Migita–Kosugi–Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . 56
3.5.1 Synthetic Methods of Organotin Compounds . . . . . . . . . 56
3.5.2 sp2–sp2 Migita–Kosugi–Stille Coupling. . . . . . . . . . . . . 57
3.5.3 Other Migita–Kosugi–Stille Couplings. . . . . . . . . . . . . . 62
3.6 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 63
3.6.1 sp2–sp2 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . 64
3.6.2 sp3–sp2 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . 69
3.7 Hiyama Coupling (sp2–sp2). . . . . . . . . . . . . . . . . . . . . . . . . . . 71
3.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74
4 Pharmaceuticals. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85
4.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85
4.2 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
4.3 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
4.4 Migita-Kosugi-Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . . 99
4.5 Kumada-Tamao-Corriu Coupling. . . . . . . . . . . . . . . . . . . . . . . 101
4.6 Sonogashira–Hagihara Coupling . . . . . . . . . . . . . . . . . . . . . . . 103
4.7 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 106
Contents ix
5 Liquid Crystals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 111
5.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 111
5.2 Kumada-Tamao-Corriu Coupling. . . . . . . . . . . . . . . . . . . . . . . 113
5.3 Migita-Kosugi-Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . . 115
5.4 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 118
5.5 Sonogashira-Hagihara Coupling. . . . . . . . . . . . . . . . . . . . . . . . 125
5.6 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 132
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133
6 Conjugated Polymers. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137
6.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137
6.2 Kumada-Tamao-Corriu Coupling. . . . . . . . . . . . . . . . . . . . . . . 138
6.3 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 144
6.4 Migita-Kosugi-Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . . 147
6.5 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 152
6.6 Sonogashira–Hagihara Coupling . . . . . . . . . . . . . . . . . . . . . . . 158
6.7 Hiyama Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166
6.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168
Part III Recent Advances in Cross-Coupling Reactions
7 Recent Advances in Cross-Coupling Reactions
with Aryl Chlorides, Tosylates, and Mesylates. . . . . . . . . . . . . . . . 177
7.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177
7.2 Kumada–Tamao–Corriu Coupling . . . . . . . . . . . . . . . . . . . . . . 178
7.3 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 180
7.4 Migita–Kosugi–Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . 182
7.5 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 184
7.6 Hiyama Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191
7.7 Sonogashira–Hagihara Coupling . . . . . . . . . . . . . . . . . . . . . . . 193
7.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 196
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 196
8 Recent Advances in Cross-Coupling Reactions
with Alkyl Halides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 203
8.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 203
8.2 Kumada-Tamao-Corriu Coupling. . . . . . . . . . . . . . . . . . . . . . . 205
8.3 Negishi Coupling. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209
8.4 Migita–Kosugi–Stille Coupling. . . . . . . . . . . . . . . . . . . . . . . . 213
8.5 Suzuki–Miyaura Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . 214
x Contents
8.6 Hiyama Coupling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221
8.7 Sonogashira–Hagihara Coupling . . . . . . . . . . . . . . . . . . . . . . . 223
8.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 225
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 225
Appendix . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231
Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239