Benziodoxole-based hypervalent iodine reagents in organic synthesis

被引:139
作者
Zhdankin, VV [1 ]
机构
[1] Univ Minnesota, Dept Chem, Duluth, MN 55812 USA
关键词
hypervalent iodine; oxidation; benziodoxole; benziodazole; IBX; DMP;
D O I
10.2174/1570179052996982
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five-membered hypervalent iodine heterocycles derived from benziodoxole and benziodazole oxide have recently emerged as reagents of choice for various synthetically useful oxidative transformations. In particular, IBX (2-iodoxylbenzoic acid) and DMP (Dess-Martin periodinane) are widely used for the selective oxidation of primary and secondary alcohols and for a variety of other important oxidations. IBX-amides and IBX-esters are a new class of pentavalent iodine reagents with a pseudo-benziodoxole structure and a reactivity pattern similar to IBX.
引用
收藏
页码:121 / 145
页数:25
相关论文
共 262 条
[1]  
Aïssa C, 2000, SYNLETT, P1585
[2]  
Akai S, 1996, HETEROCYCLES, V42, P47
[3]   SYNTHESIS AND REACTION OF SUBSTITUTED ARYLALKOXYIODINANES - FORMATION OF STABLE BROMOARYLALKOXY AND ARYLDIALKOXY HETEROCYCLIC-DERIVATIVES OF TRICOORDINATE ORGANOIODINE(III) [J].
AMEY, RL ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1779-1784
[4]  
[Anonymous], BER
[5]   STRUCTURE OF O-IODOSOBENZOIC ACID AND OF CERTAIN DERIVATIVES [J].
BAKER, GP ;
MANN, FG ;
SHEPPARD, N ;
TETLOW, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUN) :3721-&
[6]   SYNTHESIS AND STRUCTURE OF BENZIODAZOLES [J].
BALTHAZOR, TM ;
GODAR, DE ;
STULTS, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1447-1449
[7]   Synthesis of sialyl Lewis(x) mimics: Replacement of galactose by aromatic spacers [J].
Banteli, R ;
Ernst, B .
TETRAHEDRON LETTERS, 1997, 38 (23) :4059-4062
[8]   BENZIODAZOLES - SYNTHESIS FOR BIOACTIVITY STUDIES [J].
BARBER, HJ ;
HENDERSO.MA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (06) :862-&
[9]   Dess-Martin periodinane oxidation of alcohols in the presence of stabilized phosphorus ylides: A convenient method for the homologation of alcohols via unstable aldehydes [J].
Barrett, AGM ;
Hamprecht, D ;
Ohkubo, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9376-9378
[10]   Flexible and convergent total synthesis of cyclotheonamide B [J].
Bastiaans, HMM ;
vanderBaan, JL ;
Ottenheijm, HCJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3880-3889