3 years ago

Photoredox-Catalyzed C–H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen

Photoredox-Catalyzed C–H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen
Ping Wu, Xiaoge Yang, Zhengkun Yu, Quannan Wang
Visible-light-induced direct C–H arylation of S,S-functionalized internal alkenes, that is, α-oxo ketene dithioacetals and analogues, has been efficiently realized with aryldiazonium salts (ArN2BF4) as coupling partners and Ru(bpy)3Cl2·6H2O as photosensitizer at ambient temperature. The strategy to activate the internal olefinic C–H bond by both the alkylthio and electron-withdrawing functional groups was investigated. The synthetic protocol was successfully applied to the synthesis of all-carbon tetrasubstituted alkenes including tamoxifen.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03223

DOI: 10.1021/acs.orglett.7b03223

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