Table Of Content224
scipoT ni Current Chemistry
Editorial Board:
A. de Meijere • K.N. Houk. H. Kessler
].-M. Lehn- S.V. Ley. S.L. Schreiber • J. Thiem
B. M. Trost E • V6gtle • H. Yamamoto
regnirpS
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New kroY
Kong Hong
nodnoL
Milan
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tnelavrepyH Iodine yrtsimehC
Modern stnempoleveD
ni Organic sisehtnyS
Volume Editor: Thomas Wirth
With contributions by
.¥ Kita, .G E Koser, .M Ochiai, H. Tohma,
.A Varvoglis, .T Wirth, .V .V Zhdankin
r e g n~ i r p S
The series in Topics Current Chemistry presents critical reviews of the present and
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Prof. Dr. Armin de Meijere Prof. K.N. Houk
Institut Organische ffir Chemie Department of Chemistry and Biochemistry
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The pioneers of hypervalent iodine chemistry have already realized that the
chemistry of iodine(u1) and iodine(v)-containing compounds offers multiple
advantages over established methods. A wide range of reactions is possible,
oxidations and C-C-coupling reactions under extremely mild reaction condi-
tions and with a broad tolerance of other functional groups being the most
prominent ones. The various findings in, and applications of, the chemistry with
hypervalent iodine compounds has led, in recent years, to a tremendous growth
which is reflected by the large number of publications in this field. However,
the last comprehensive compilation of hyper valent iodine chemistry appeared
morteh an five years ago. We felt that there a is need for an update. I am grateful
to the distinguished scientists, who contributed, with their skill and expertise,
thvea rious chapters of this volume. By emphasizing the developments in hyper-
valent iodine chemistry over the last couple of years, this volume presents a
comprehensive overview of the various facets, scope, and limitations of organic
chemistry with hypervalent iodine compounds.
Cardiff, July 2002 Thomas Wirth
stnetnoC
Introduction and Aspects General
T. Wirth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Reactivities, Properties and Structures
M. Ochiai . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Preparation of Hypervalent Iodine Compounds
A. Varvoglis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
C-C Bond Forming Reactions
V.V. Zhdankin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99
C-Heteroatom-Bond Forming Reactions
G. E Koser . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137
Heteroatom-Heteroatom-Bond Forming Reactions
G.E Koser . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173
Oxidations and Rearrangements
.T Wirth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185
Synthetic Applications Synthesis (Total and Natural Product Synthesis)
H. Tohma, .Y Kita . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209
Author Index Volumes 201-224 . . . . . . . . . . . . . . . . . . . . . . . 249
Subject Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 257
stnetnoC of Volume 208
muinelesonagrO yrtsimehC
Modern stnempoleveD in cinagrO sisehtnyS
Volume Editor: Thomas Wirth
ISBN 3-540-66516-1
Introduction and GeneralA spects
.T Wirth
Electrophilic SeleniuSme,l enocyclizations
M. Tiecco
Nucleophilic Selenium
M. Iwaoka, .S Tomoda
Radical Reactions Using Selenium Precursors
.P Renaud
Selenium-Stabilized Carbanions
.S Ponthieux, .C Paulmier
Selenium at Higher Oxidation States
.J Drabowicz, M. Mikohjczyk
Selenocarbonyls
.T Mural, .S Kato
Selenoxide Elimination and [2,3] Sigmatropic Rearrangements
.Y Nishibayashi, .S Uemura
Selenium Compounds as Ligands and Catalysts
¥. Nishibayashi, .S Uemura
Introduction and General Aspects
Thomas Wirth
Department ofChemistry,CardiffUniversity,PO Box 912,CardiffCF10 3TB,UK
E-mail:[email protected]
Recent progress on hypervalent iodine chemistry is summarized in this book.
Keywords. Hypervalent iodine chemistry
Hypervalent iodine reagents were discovered a long time ago and (dichloro-
iodo)benzene as the first member of this class was prepared by Willgerodt in
1886 [1].He was also the author ofthe first comprehensive book in this field in
1914 [2]. A growing interest in the chemistry with these compounds was
observed about 60 years later, although some reviews on hypervalent iodine
compounds were published as early as in the 1960s [3, 4]. Several reviews
appeared between then and 1990 [5–17] and these are summarized in Table1.
Recently many more reviews have been published on various parts of hyper-
valent iodine chemistry [18–29] and several books [30–32] on this topic have
appeared covering many aspects ofthese reagents.
The purpose ofthis book is to address and summarize recent developments
and synthetic applications in the field of hypervalent iodine chemistry.There-
fore,emphasis is placed on the post 1990s literature with reference to earlier
work where necessary and appropriate.
The concept ofhypervalent molecules was established in 1969 [33].Molecules
containing elements ofGroups 15–18 bearing more electrons than the octet in
the valence shell are described as hypervalent molecules.Descriptions of such
systems using molecular orbital theory led to the proposal of 3-center-4-elec-
tron (3c–4e) bonds (hypervalent bonds) [34,35].Supported by computational
work this concept is now generally accepted [36,37].Its application to iodanes is
detailed at the beginning ofthe chapter Structures,Properties and Reactivities
by M.Ochiai.The most common hypervalent iodine compounds are aryl-l3-
iodanes (ArIL ) with a decet structure and pseudotrigonal bipyramidal geome-
2
tries and aryl-l5-iodanes (ArIL ) with a dodecet structure and square pyrami-
4
dal geometries.The nomenclature for these molecules is not satisfactory and
several names for the same compound are often in use.Therefore,throughout
this book various names and abbreviations for the hypervalent iodine reagents
have been used by the authors as we have not applied the sometimes lengthy
IUPAC names.As we have tried to outline general principles and synthetic con-
cepts in this book, the chapter by M. Ochiai describes the theoretical back-
ground ofhypervalent iodine reagents as well as giving examples oftheir reac-
Topics in Current Chemistry,Vol.224
© Springer-Verlag Berlin Heidelberg 2003
