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铑催化的氟化烯烃环丙烷化反应:通往高官能化氟代环丙烷的直接途径。

Rhodium-catalyzed cyclopropanation of fluorinated olefins: a straightforward route to highly functionalized fluorocyclopropanes.

作者信息

Pons Amandine, Beucher Hélène, Ivashkin Pavel, Lemonnier Gérald, Poisson Thomas, Charette André B, Jubault Philippe, Pannecoucke Xavier

机构信息

†Normandie Université, COBRA, UMR 6014 et FR 3038, Université Rouen, INSA Rouen, CNRS, 1 rue Tesnière, Mont Saint-Aignan 76821 Cedex, France.

‡Centre in Green Chemistry and Catalysis, Faculty of Arts and Sciences, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.

出版信息

Org Lett. 2015 Apr 3;17(7):1790-3. doi: 10.1021/acs.orglett.5b00576. Epub 2015 Mar 13.

Abstract

An efficient access to highly functionalized monofluorocyclopropanes is described. The developed methodology allowed straightforward access to a large panel of polysubstituted fluorinated cyclopropanes in good to excellent yields and good diastereoselectivities. The Rh-catalyzed cyclopropanation proved to be efficient on several fluorinated olefins and several diazo compounds. This method represents the first general route to complex fluorinated cyclopropanes.

摘要

本文描述了一种高效合成高官能化单氟环丙烷的方法。所开发的方法能够直接合成大量多取代的氟化环丙烷,产率良好至优异,非对映选择性也较好。铑催化的环丙烷化反应在几种氟化烯烃和几种重氮化合物上均证明是有效的。该方法代表了合成复杂氟化环丙烷的第一条通用路线。

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