Rapid Access to β??Trifluoromethyl??Substituted Ketones: Harnessing Inductive Effects in Wacker??Type Oxidations of Internal Alkenes

…, B Morandi, ZK Wickens, RH Grubbs

Index: Wickens, Zachary K.; Morandi, Bill; Grubbs, Robert H. Angewandte Chemie - International Edition, 2013 , vol. 52, # 43 p. 11257 - 11260 Angew. Chem., 2013 , vol. 125, # 43 p. 11467 - 11470

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Citation Number: 11

Abstract

Abstract We present a practical trifluoromethyl-directed Wacker-type oxidation of internal alkenes that enables rapid access to β-trifluoromethyl-substituted ketones. Allylic trifluoromethyl-substituted alkenes bearing a wide range of functional groups can be oxidized in high yield and regioselectivity. The distance dependence of the regioselectivity was established by systematic variation of the number of methylene units between the ...