Gold-Catalyzed, Iodine(III)-Mediated Direct Acyloxylation of the Unactivated C(sp3)-H Bonds of Methyl Sulfides

The gold‐catalyzed, iodine(III)‐mediated direct oxidative acyloxylation of the C(sp3)–H bonds of methyl sulfides for the synthesis of various α‐thioaryl and α‐thioalkyl ester derivatives was discovered. Bis(acyloxy)iodobenzene proved to be an efficient reagent to activate the sulfur atom as an in si...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2016-09, Vol.2016 (25), p.4260-4264
Main Authors: Guo, Sheng-rong, Santhosh Kumar, Pailla, Yuan, Yan-qin, Yang, Ming-hua
Format: Article
Language:English
Subjects:
Acyloxylation
C-H activation
Gold
Hypervalent compounds
Iodine
Sulfur
Synthetic methods
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 gold‐catalyzed, iodine(III)‐mediated direct oxidative acyloxylation of the C(sp3)–H bonds of methyl sulfides for the synthesis of various α‐thioaryl and α‐thioalkyl ester derivatives was discovered. Bis(acyloxy)iodobenzene proved to be an efficient reagent to activate the sulfur atom as an in situ directing group for α‐C(sp3)–H functionalization. The attractive features of this protocol include short reaction times, low catalyst loading, and in situ activation of adjacent C(sp3)–H bonds of the sulfur atom. An efficient reaction for the iodine(III)‐mediated acyloxylation of the unactivated C(sp3)–H bonds of methyl sulfides is reported. This strategy utilizes various hypervalent iodine reagents and involves an ionic pathway to deliver the desired products in excellent yields (DCE = 1,2‐dichloroethane).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600632