A late-stage functionalization tool: sulfonyl fluoride mediated deoxymethylation of phenols. Issue 38 (20th September 2022)

• Record Type: Journal Article
• Authors: Zhang, Guofu; Guan, Chenfei; Han, Linjun; Zhao, Yiyong; Ding, Chengrong
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 38(2022)
• Page Start: 7640
• Page End: 7644
• Publication Date: 2022-09-20
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01523d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient and rapid phenol deoxymethylation strategy without purification during the reaction is reported. This protocol has tolerance for a wide range of functional groups and high yields making it successful for application in LSF. Abstract : The late-stage functionalization of drugs and natural products has been identified as a promising approach to accelerate the discovery of new bioactive compounds. Due to the presence of the "Magic Methyl Effect", the direct deoxymethylation of phenolic hydroxyl groups, which are widespread in natural molecules, is a challenging task. A mild and rapid strategy for direct phenol deoxymethylation under metal catalysis using SO2 F2 is described in this paper, while good functional group tolerance and high chemoselectivity allow this strategy to be one of the powerful tools for LSF. The power of this new platform is showcased through gram-scale and orthogonal experiments.