Introduction of Cyclopropyl and Cyclobutyl Ring on Alkyl Iodides through Cobalt-Catalyzed Cross-Coupling

被引：25

作者：

Andersen, Claire ^{[1
]}

Ferey, Vincent ^{[2
]}

Daumas, Marc ^{[3
]}

Bernardelli, Patrick ^{[4
]}

Guerinot, Amandine ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] PSL Univ, Mol Macromol Chem & Mat, ESPCI Paris, CNRS, 10 Rue Vauquelin, F-75005 Paris, France

[2] Sanofi R&D, 371 Rue Prof Joseph Blayac, F-34080 Montpellier, France

[3] Sanofi Chim, Route Avignon, F-30390 Aramon, France

[4] Sanofi R&D, 1 Ave Pierre Brossolette, F-91380 Chilly Mazarin, France

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

关键词：

ARYL GRIGNARD-REAGENTS; 6-HALO-1-HEXENE DERIVATIVES; HALIDES; SECONDARY; STRATEGIES; INHIBITORS; ARYLATION;

D O I：

10.1021/acs.orglett.9b00579

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cobalt-catalyzed cross-coupling between alkyl iodides and cyclopropyl, cyclobutyl, and alkenyl Grignard reagents is disclosed. The reaction allows the introduction of strained rings on a large panel of primary and secondary alkyl iodides. The catalytic system is simple and nonexpensive, and the reaction is general, chemoselective, and diastereoconvergent. The alkene resulting from the cross-coupling can be transformed to substituted cyclopropanes using a Simmons-Smith reaction. The formation of radical intermediates during the coupling is hypothesized.

引用

页码：2285 / 2289

页数：5

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