Direct Sulfenylation of the Purine C8-H Bond with Thiophenols

Wei Jiang; Juanping Zhuge; Jianxiao Li; Gary Histand; Dongen Lin

doi:10.1021/acs.joc.9b03115

Direct Sulfenylation of the Purine C₈-H Bond with Thiophenols

J Org Chem. 2020 Feb 21;85(4):2415-2425. doi: 10.1021/acs.joc.9b03115. Epub 2020 Jan 14.

Authors

Wei Jiang¹, Juanping Zhuge¹, Jianxiao Li¹, Gary Histand², Dongen Lin¹

Affiliations

¹ Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510641 , P. R. China.
² International School of Advanced Materials , South China University of Technology , Guangzhou 510640 , P. R. China.

PMID: 31898455
DOI: 10.1021/acs.joc.9b03115

Abstract

The one-step copper-mediated regioselective formation of the C₈-S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na₂CO₃ and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-handle, and effective method for the synthesis of 8-sulfenylpurine derivatives in moderate to excellent yields. The reaction is selective for C8 over C2 and C6. It also tolerates a free amine on the purine, and it has a wide substrate scope.

Publication types

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