Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C=N double bonds

被引:24
作者
Cougnon, Fabien
Feray, Laurence [1 ]
Bazin, Samantha
Bertrand, Michele P. [1 ]
机构
[1] Univ Paul Cezanne, Fac Sci St Jerome, UMR 6517, Lab Chim Mol Organ, F-13397 Marseille, France
关键词
alkyl phenyl telluride; diethylzinc; dimethylzinc; radical addition to imino group;
D O I
10.1016/j.tet.2007.09.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diethylzinc-mediated radical addition to C=N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of diethylzinc by dimethylzinc, offers no advantage in these reactions. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11959 / 11964
页数:6
相关论文
共 58 条
[1]   Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air [J].
Akindele, Tito ;
Yamamoto, Yasutomo ;
Maekawa, Masaru ;
Umeki, Hiroyuki ;
Yamada, Ken-ichi ;
Tomioka, Kiyoshi .
ORGANIC LETTERS, 2006, 8 (25) :5729-5732
[2]   Nickel-catalysed addition of dialkylzinc reagents to N-phosphinoyl- and N-sulfonylimines [J].
Almansa, Raquel ;
Guijarro, David ;
Yus, Miguel .
TETRAHEDRON, 2007, 63 (05) :1167-1174
[3]   α,β-Unsaturated diesters:: radical acceptors in dialkylzinc-mediated tandem radical addition/aldol condensation.: A straightforward synthesis of rac-nephrosteranic acid [J].
Bazin, Samantha ;
Feray, Laurence ;
Vanthuyne, Nicolas ;
Siri, Didier ;
Bertrand, Michele P. .
TETRAHEDRON, 2007, 63 (01) :77-85
[4]   Dialkylzincs in radical reactions [J].
Bazin, Samantha ;
Feray, Laurence ;
Bertrand, Michele P. .
CHIMIA, 2006, 60 (05) :260-265
[5]   Diethylzinc: A chain-transfer agent in intermolecular radical additions. A parallel with triethylborane [J].
Bertrand, MP ;
Feray, L ;
Nouguier, R ;
Perfetti, P .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) :9189-9193
[6]  
Bertrand MP, 1999, SYNLETT, P1148
[7]   Et3B- and Et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions [J].
Bertrand, MP ;
Coantic, S ;
Feray, L ;
Nouguier, R ;
Perfetti, P .
TETRAHEDRON, 2000, 56 (24) :3951-3961
[8]  
BERTRAND MP, 2002, CR CHIM, P623
[9]   ORGANIC TELLURIUM AND SELENIUM CHEMISTRY - REDUCTION OF TELLURIDES, SELENIDES, AND SELENOACETALS WITH TRIPHENYLTIN HYDRIDE [J].
CLIVE, DLJ ;
CHITTATTU, GJ ;
FARINA, V ;
KIEL, WA ;
MENCHEN, SM ;
RUSSELL, CG ;
SINGH, A ;
WONG, CK ;
CURTIS, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4438-4447
[10]   PHOTOINDUCED FREE-RADICAL CHEMISTRY OF THE ACYL TELLURIDES - GENERATION, INTERMOLECULAR AND INTRAMOLECULAR TRAPPING, AND ESR SPECTROSCOPIC IDENTIFICATION OF ACYL RADICALS [J].
CRICH, D ;
CHEN, C ;
HWANG, JT ;
YUAN, HW ;
PAPADATOS, A ;
WALTER, RI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :8937-8951