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Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S-S Bond

Nobukazu Taniguchi

*Department of Chemistry, Fukushima Medical University, Fukushima 960-1295, Japan, Email: tanigutifmu.ac.jp

N. Taniguchi, J. Org. Chem., 2006, 71, 7874-7876.

DOI: 10.1021/jo060834l (free Supporting Information)



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Abstract

A regio and anti-selective copper-catalyzed 1,2-hydroxysulfenylation of alkenes can be carried out by the use of disulfides and acetic acid. Reoxidation of intermediate sulfides by oxygen enables the use of both organosulfide groups of the disulfides.


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proposed mechanism



Convenient Synthesis of Unsymmetrical Organochalcogenides Using Organoboronic Acids with Dichalcogenides via Cleavage of the S-S, Se-Se, or Te-Te Bond by a Copper Catalyst

N. Taniguchi, J. Org. Chem., 2007, 72, 1241-1245.


Key Words

Sulfides, Arylsulfides, Oxygen


ID: J42-Y2006-3050