title: Nickel-Catalyzed Regioselective Cleavage of C(sp(2))-S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes.
abstract: We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H2O2 as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Jinyang
authors.initials: J
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Sihai
authors.initials: S
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Xinhua
authors.initials: X
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Tang
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Chak-Tong
authors.initials: CT
authors.lastname: Au
authors.affiliation: State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha, 410082, People's Republic of China.
authors.forename: Renhua
authors.initials: R
authors.lastname: Qiu