Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate

Hideyuki Konishi; Hiromichi Tanaka; Kei Manabe

doi:10.1021/acs.orglett.7b00402

Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K₂S₂O₅ as a Sulfur Dioxide Surrogate

Org Lett. 2017 Apr 7;19(7):1578-1581. doi: 10.1021/acs.orglett.7b00402. Epub 2017 Mar 9.

Authors

Hideyuki Konishi¹, Hiromichi Tanaka¹, Kei Manabe¹

Affiliation

¹ School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

PMID: 28277668
DOI: 10.1021/acs.orglett.7b00402

Abstract

A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO₂) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.

Publication types

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