Cross-Coupling Reactions: A Practical Guide

252 Pages·2002·3.948 MB·English

by  Tamao Kohei, Norio Miyaura (auth.), Prof. Norio Miyaura (eds.)

219
scipoT ni Current yrtsimehC
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].-M. Lehn. S.V. Ley. S.L. Schreiber • J. Thiem
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Berlin
Heidelberg
New kroY
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Kong Hong
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Milan
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Practical A Guide
e m u l o V :rotidE oiroN a r u a y i M
With contributions by
.L .S Buchwald, .K Fugami, .T Hiyama, .M Kosugi,
M. Miura, N. Miyaura, A. .R Muci, M. Nomura,
.E Shirakawa, .K Tamao
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.forP Norio Miyaura
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Preface
In 1972,a very powerful catalytic cycle for carbon-carbon bond formation was
first discovered by the coupling reaction ofGrignard reagents at the sp2-carbon.
Over the past 30 years, the protocol has been substantially improved and
expanded to other coupling reactions ofLi,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn,
and Hg compounds. These reactions provided an indispensable and simple
methodology for preparative organic chemists.Due to the simplicity and relia-
bility in the carbon-carbon,carbon-heteroatom,and carbon-metalloid bond-
formations,as well as high efficiency ofthe catalytic process,the reactions have
been widely employed by organic chemists in various fields.Application ofthe
protocol ranges from various syntheses of complex natural products to the
preparation of biologically relevant molecules including drugs,and of supra-
molecules,and to functional materials.The reactions on solid surfaces allow
robot synthesis and combinatorial synthesis.Now,many organic chemists do
not hesitate to use transition metal complexes for the transformation oforgan-
ic molecules.Indeed,innumerable organic syntheses have been realized by the
catalyzed reactions oftransition metal complexes that are not achievable by tra-
ditional synthetic methods.Among these, the metal-catalyzed cross-coupling
reactions have undoubtedly contributed greatly to the development of such a
new area of “metal-catalyzed organic syntheses”.
An excellent monograph for the cross-coupling reactions and other metal-
catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed
Cross-coupling Reactions(Wiley-VCH,1998).In order to avoid overlapping with
previous publications,also in view ofspace limitation,this book is restricted to
the most recent and practical developments in this field.The book covers new
advances in the representative coupling reactions oforganoboron,-silicon,and
-tin compounds,as well as two new areas for carbon-heteroatom bond forma-
tion and the carbon-carbon bond formation via direct C-H substitution.The
actual practical procedures ofthe cross-coupling reactions are given,including
technical advice on actual applications in organic synthesis.The hope of the
authors is that this book will help both expert and novice practitioners to use
metal-catalyzed cross-reactions for organic syntheses.
Sapporo,October 2001 Norio Miyaura
Contents
Introduction to Cross-Coupling Reactions
K. Tamao, N. Miyaura ............................. 1
Organoboron Compounds
N. Miyaura .................................. 11
OrganosiUcon Compounds
.T Hiyama, E. Shirakawa ........................... 61
Organotin Compounds
K. Fugami, M. Kosugi ............................. 87
Practical Palladium Catalysts for C-N and C-O Bond Formation
RA.. Muci, S.L. Buchwald ........................... 131
Direct Arylation via Cleavage of Activated and Unactivated C-H Bonds
M. Miura, M. Nomura ............................. 211
Author Index Volumes 201-219 ....................... 243
Contents of Volume 191
cinortcelE and Spectra Vibronic
of Transition Metal sexelpmoC II
Volume Editor: H. Yersin
ISBN 3-540-62922-X
Spectroscopy of the Sublevels Spin of Transition Complexes Metal
.T Azumi, .H Miki
Magnetic and Spectroscopic Properties of Os2(Os2CR)4C12 .
Evidence for a3(6" n*) Ground State
.V .M Miskowski, .H .B Gray
Luminescence and Absorption Studies of Transition Metal Ions
in Host Crystals, Pure Crystals and Surface Environments
Patterson H.H.
Angular Applied Model Overlap to Transition Complexes Metal
and dS-lons in Host Lattices Oxide
.T Sch6nherr
Characterization of Excited Electronic and Vibronic States of Platinum Metal
Compouwnidtsh Ligands Chelate by Highly Frequency-Resolved
and Time-Resolved Spectra
.H ,nisreY .W Humbs, .J Strasser
Introduction to Cross-Coupling Reactions
Kohei Tamao1,Norio Miyaura2
1 Institute for Chemical Research,Kyoto University Uji,Kyoto 611-0011,Japan
E-mail:tamao @sc1.kyoto-u.ac.jp
2 Division ofMolecular Chemistry,Graduate School ofEngineering,Hokkaido University,
Sapporo 060-8628,Japan
E-mail:[email protected]
1 Historical Perspective . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
2 Catalytic Cycle . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
3 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7
1
Historical Perspective
The cross-coupling reaction of organometallic reagents with organic elec-
trophiles in the presence ofgroup 8–10 metal catalysts,notably nickel and pal-
ladium complexes,is the method of choice for a wide range of C-C,C-H,C-N,
C-O,C-S,C-P or C-M bond-forming process [1].These reactions,now accessible
with a variety oforganometallic reagents and electrophiles,provide a common
class of synthetic transformations, commonly referred to as “cross-coupling
reactions”(Eq.1).
(1)
The reactions of Li/Mg reagents in the presence of stoichiometric and
catalytic amounts of copper halides had been studied extensively during the
1960’s to 1970’s [2].The reaction at sp2- or sp-carbons,however,was very limit-
ed until the discovery ofthe transition metal-catalyzed cross-coupling reaction
ofGrignard reagents.In 1971,Kochi reported the efficiency ofFeCl as a catalyst
3
for the coupling ofGrignard reagents with 1-alkenyl bromides [3] and Li CuCl
2 4
Topics in Current Chemistry,Vol.219
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