Ruthenium(II)-Catalyzed C-H Arylation of N,N-Dialkyl Thiobenzamides with Boronic Acids by Sulfur Coordination in 2-MeTHF

Jin Zhang; Ying Liu; Qiangqiang Jia; Yue Wang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.0c02410

Ruthenium(II)-Catalyzed C-H Arylation of N,N-Dialkyl Thiobenzamides with Boronic Acids by Sulfur Coordination in 2-MeTHF

Org Lett. 2020 Sep 4;22(17):6884-6890. doi: 10.1021/acs.orglett.0c02410. Epub 2020 Aug 18.

Authors

Jin Zhang¹, Ying Liu¹, Qiangqiang Jia², Yue Wang¹, Yangmin Ma¹, Michal Szostak^{1

3}

Affiliations

¹ College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Additives for China National Light Industry, Shaanxi University of Science and Technology, Xi'an 710021, China.
² State Key Laboratory of Plateau Ecology and Agriculture, Qinghai University, Xining 810016, China.
³ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

PMID: 32809838
DOI: 10.1021/acs.orglett.0c02410

Abstract

We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl₂(p-cym)]₂ in the presence of Cu(OTf)₂ and Ag₂O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.

Publication types

Research Support, Non-U.S. Gov't