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银催化的 C(sp^2)-H 氯化反应。

Silver-Catalyzed C(sp)-H Chlorination.

机构信息

Graduate School of Pharmaceutical Sciences, The University of Tokyo , Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

JST, ERATO , Kanai Life Science Catalysis Project, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

出版信息

Org Lett. 2017 Mar 17;19(6):1430-1433. doi: 10.1021/acs.orglett.7b00367. Epub 2017 Mar 3.

Abstract

A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.

摘要

发展了一种银催化的苄位、叔位和仲 C(sp)-H 键的氯化反应。该反应在室温下、空气氛围中、以低至 0.2 mol%的催化剂负载量进行,具有合成上有用的官能团相容性。区域选择性和反应性趋势表明氯化反应是通过自由基途径进行的,但不能排除烷基银中间体的存在。

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