Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones

Guichun Fang; Jianquan Liu; Weidong Shang; Qun Liu; Xihe Bi

doi:10.1002/asia.201601223

Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones

Chem Asian J. 2016 Dec 6;11(23):3334-3338. doi: 10.1002/asia.201601223. Epub 2016 Nov 16.

Authors

Guichun Fang¹, Jianquan Liu¹, Weidong Shang¹, Qun Liu¹, Xihe Bi^{1

2}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Renmin Str. 5268#, Changchun, 130024, China.
² State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.

PMID: 27860354
DOI: 10.1002/asia.201601223

Abstract

An efficient Ag₂ CO₃ -promoted sulfonylation of allyl/propargyl alcohols with sodium sulfinates has been developed. The reaction tolerates a wide range of functional groups to deliver γ-keto sulfones in high yields (up to 93 %). Propargyl alcohols furnished trimerization product 1,3,5-triaroylbenzenes in the presence of sodium methanesulfinate under the standard conditions. A mechanism involving a sulfonyl radical was suggested.

Keywords: allyl/propargyl alcohols; gamma-keto sulfones; radical sulfonylation; reaction mechanisms; silver catalysis.