Solvent-Controlled, Tunable β-OAc and β-H Elimination in Rh(III)-Catalyzed Allyl Acetate and Aryl Amide Coupling via C–H Activation

• DOI: 10.1021/acs.orglett.6b01566
• Publication Date: 2016-06-28T12:31:19Z
• Authors: Huimin Dai; Chao Yu; Zihao Wang; Hong Yan; Changsheng Lu
• Keywords: 01 natural sciences; 0104 chemical sciences

The Heck reaction between arenes and allyl acetate has led to cinnamyl derivatives and allyl products depending on the regioselectivity of β-elimination. The regioselectivity can be controlled by the solvent in the Rh(III)-catalyzed arene-allyl acetate coupling via C-H activation: (1) in THF, cinnamyl derivatives via β-H elimination were generated; (2) in MeOH, allyl products via β-OAc elimination were produced. Both routes have advantages such as excellent γ-selectivity toward allyl acetate, good to excellent yields, and broad substrate scope.