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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Published on: July 28, 2018

Complementary C-H Functionalization Mode of Benzoylacetonitriles: Computer-Augmented Study of a Regio- and

Xia Song¹, Bao Nguyen Do Doan², Xinying Zhang¹

¹Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Environment, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.

Organic Letters

|December 24, 2019

Abstract:

A highly regio- and stereoselective synthesis of functionalized benzofulvenes via Rh(III)-catalyzed cascade reactions of benzoyl acetonitrile/methylsulfone/acetate with propargyl alcohols is presented herein. Mechanistic modeling performed with density functional theory (DFT) calculations suggested that the hydroxyl group and CsOAc played important roles in mediating the 5-membered ring cyclization by forming a very thermodynamically stable Rh(III) intermediate. Another remarkable feature of this transformation is its excellent stereoselectivity in that only E-isomers are obtained.

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