30911-16-1Relevant articles and documents
Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling
Xu, Hehuan,Liu, Jiayu,Nie, Feiyun,Zhao, Xiaowei,Jiang, Zhiyong
, p. 16204 - 16212 (2021/10/25)
An electrochemical hydropyridylation of thioester-activated alkenes with 4-cyanopyridines has been developed. The reactions experience a tandem electroreduction of both substrates on the cathode surface, protonation, and radical cross-coupling process, resulting in a variety of valuable pyridine variants, which contain a tertiary and even a quaternary carbon at the α-position of pyridines, in high yields. The employment of thioesters to the conjugated alkenes enables no requirement of catalyst and high temperature, representing a highly sustainable synthetic method.
Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters
Gehrtz, Paul H.,Kathe, Prasad,Fleischer, Ivana
supporting information, p. 8774 - 8778 (2018/06/26)
The Pd-catalyzed Fukuyama reaction of thioesters with organozinc reagents is a mild, functional-group-tolerant method for acylation chemistry. Its Ni-catalyzed variant might be a sustainable alternative to expensive catalytic Pd sources. We investigated the reaction of S-ethyl thioesters with aryl zinc halides with hetero- and homotopic Ni precatalysts and several ligands. The results show that both homo- and heterotopic species may contribute to catalysis. The substrate scope using an operationally homogeneous defined Ni complex was established. Acyl radicals are postulated as short-lived intermediates.
Conjugate reduction and reductive aldol cyclization of α,β- unsaturated thioesters catalyzed by (BDP)CuH
Li, Ninglin,Ou, Jun,Miesch, Michel,Chiu, Pauline
, p. 6143 - 6147 (2011/10/08)
A conjugate reduction of α,β-unsaturated thioesters catalyzed by copper hydride using PMHS as stoichiometric reductant has been developed. 1,2-Bis(diphenylphosphino)benzene (BDP) was the most effective ligand for this reduction. Saturated thioesters could be produced in excellent yields when the substituent on the thiol is not sterically-demanding. This protocol was applied to induce the reductive aldol cyclization of keto-enethioates, which could offer β-hydroxythioesters in moderate to good yields.