Nickel-catalyzed Thioester Transfer Reaction with sp2-Hybridized Electrophiles

Xiaopeng Wu; Jinhang Li; Siyu Xia; Chengjian Zhu; Jin Xie

doi:10.1021/acs.joc.2c00979

Nickel-catalyzed Thioester Transfer Reaction with sp²-Hybridized Electrophiles

J Org Chem. 2022 Aug 5;87(15):10003-10017. doi: 10.1021/acs.joc.2c00979. Epub 2022 Jul 10.

Authors

Xiaopeng Wu¹, Jinhang Li¹, Siyu Xia¹, Chengjian Zhu^{1

2

3}, Jin Xie^{1

4}

Affiliations

¹ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China.
³ College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China.
⁴ State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, China.

PMID: 35815594
DOI: 10.1021/acs.joc.2c00979

Abstract

We report a thioacylation transfer reaction based on nickel-catalyzed C-C bond cleavage of thioesters with sp²-hybridized electrophiles. Aryl bromides, iodides, and alkenyl triflates can participate in thioester transfer reaction of aryl thioesters, affording a wide range of structurally diverse new thioesters in yields of up to 98% under mild reaction conditions. With this protocol, it is possible to construct alkenyl thioesters from the corresponding ketones through the generation of alkenyl triflates.