Direct Sulfenylation of the Purine C 8 -H Bond with Thiophenols

The one-step copper-mediated regioselective formation of the C -S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na CO and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-han...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2020-02, Vol.85 (4), p.2415-2425
Main Authors: Jiang, Wei, Zhuge, Juanping, Li, Jianxiao, Histand, Gary, Lin, Dongen
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The one-step copper-mediated regioselective formation of the C -S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na CO 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03115