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Published on: June 21, 2017
Direct α-C-H Alkylation of Alcohols with Alkenes
Lilan Duan1, Yutao Shi1, Xiaochen Ji1
1Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
None:
Herein, we report a direct α-C-H alkylation of alcohols with alkenes enabled by organic photoredox catalysis, in which the additive trimethylsilyl azide (TMSN3) plays a crucial role in the selective activation of the α-C-H bond of free alcohols. Both α-CF3-alkenes and acrylamides showed high efficiency and excellent chemoselectivity in this transformation, affording various γ-trifluoromethyl alcohols and γ-hydroxyl amides under mild conditions. The late-stage modification of several drug derivatives was achieved, and the synthetic utility of this protocol was further highlighted by the scaled-up reaction and several derivations of the products.
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