SmI2-mediated sequential radical cyclization/anionic capture of aryl iodides on solid support

被引:48
作者
Du, XH [1 ]
Armstrong, RW [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)00292-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryl radicals were generated by SmI2 on solid support, cyclized on to C=C bond, and reduced to their organosamarium anionic species followed by electrophilic capture. However, the capture reaction was substrate-dependant in solution and on solid support. In some examples, results from solid phase reactions were equal or better to the corresponding solution reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2281 / 2284
页数:4
相关论文
共 13 条
[1]  
[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]   Synthesis of prostaglandin E-2 methyl ester on a soluble-polymer support for the construction of prostanoid libraries [J].
Chen, SQ ;
Janda, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (37) :8724-8725
[4]  
CURRAN DP, 1990, SYNLETT, P773
[5]   THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].
CURRAN, DP ;
TOTLEBEN, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058
[6]   Synthesis of benzofuran derivatives on solid support via SmI2-mediated radical cyclization [J].
Du, XH ;
Armstrong, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5678-5679
[7]   Organic chemistry on solid supports [J].
Fruchtel, JS ;
Jung, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42
[8]   Solid-phase organic reactions: A review of the recent literature [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, D .
TETRAHEDRON, 1996, 52 (13) :4527-4554
[9]   Sequencing reactions with samarium(II) iodide [J].
Molander, GA ;
Harris, CR .
CHEMICAL REVIEWS, 1996, 96 (01) :307-338
[10]   REDUCTIVE RADICAL CYCLIZATIONS OF HALOALKENES PROMOTED BY SAMARIUM DIIODIDE - SEQUENTIAL CYCLIZATION INTERMOLECULAR CARBONYL ADDITION-REACTIONS [J].
MOLANDER, GA ;
HARRING, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6171-6176