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Carboxyl‐Directed Conjugate Addition of C‒H Bonds to α,ß‐Unsaturated Ketones in Air and Water

A simple ruthenium‐catalyzed conjugate addition of C‒H bonds to α,ß‐unsaturated ketones directed by a removable carboxyl group was developed as an effective protocol to synthesize ortho‐alkylated benzoic acids in a greener manner. Without any additives, satisfactory to excellent yields of the targeted products were achieved in neat water, and the process characterizes in mild reaction conditions (in air and water), simple operations, and broad substrate scope. Noteworthy features of this method include mild reaction conditions (in air and water), operational simplicity and broad substrate scope. The versatility and utility of the addition products were demonstrated through further transformation into commonly inaccessible but highly useful motifs of meta‐substituted alkylbenzenes and 3‐substituted isochromanones.

Authors:   Wen-jing Han, Fan Pu, Chao-Jun Li, Zhong-Wen Liu, Juan Fan, Xian-Ying Shi
Journal:   Advanced Synthesis & Catalysis
Year:   2018
Pages:   n/a
DOI:   10.1002/adsc.201701468
Publication date:   19-Jan-2018
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