Cyclopropylmethylation of Benzylic and Allylic Chlorides with Cyclopropylmethylstannane Catalyzed by Gallium or Indium Halide

被引：15

作者：

Kiyokawa, Kensuke ^{[1
]}

Yasuda, Makoto ^{[1
]}

Baba, Akio ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Ctr Atom & Mol Technol, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

SIGMA-PI CONJUGATION; CYCLOPROPANE DERIVATIVES; ELECTROPHILIC CLEAVAGE; CARBON ELECTROPHILES; ORGANIC-SYNTHESIS; RADICAL-ADDITION; OLEFINS; CYCLIZATION; HOMOALLYLSTANNANES; CHLORINATION;

D O I：

10.1021/ol100240b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzylic and allylic chlorides easily coupled with cyclopropylmethylstannane in the presence of GaCl(3) or InBr(3) catalyst, in which an intermediate of an active butenylgallium or -indium species was confirmed by NMR spectroscopy and X-ray analysis. An ionic reaction process is plausible for this coupling.

引用

页码：1520 / 1523

页数：4

共 36 条

[1] REACTIONS OF CYCLOPROPYLCARBINYL HALIDES WITH (TRIMETHYLSTANNYL)ALKALIS - EVIDENCE THAT KINETICALLY FREE INTERMEDIATES NEED NOT BE INVOLVED IN CYCLOPROPYLCARBINYL TO 3-BUTENYL REARRANGEMENTS [J].