title: Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones.
abstract: A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Zhen
authors.initials: Z
authors.lastname: He
authors.affiliation: School of Chemistry and Chemical Engineering, Chongqing University , Chongqing 400030, P. R. China.
authors.forename: Xiaotian
authors.initials: X
authors.lastname: Qi
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Zhijie
authors.initials: Z
authors.lastname: She
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Yinsong
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Shiqing
authors.initials: S
authors.lastname: Li
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Junbin
authors.initials: J
authors.lastname: Tang
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Ge
authors.identifier: 0000-0001-9980-7311
authors.initials: G
authors.lastname: Gao
authors.affiliation: School of Chemistry and Chemical Engineering, Chongqing University , Chongqing 400030, P. R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Lan
authors.affiliation: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University 29 Wangjiang Road, Chengdu 610064, P. R. China.
authors.forename: Jingsong
authors.identifier: 0000-0002-0493-2388
authors.initials: J
authors.lastname: You