Organic Chemistry Portal

Abstracts

Search:

Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols

Noriaki Shohji, Tsuyoshi Kawaji and Sentaro Okamoto*

*Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan, Email: okamos10kanagawa-u.ac.jp

N. Shohji, T. Kawaji, S. Okamoto, Org. Lett., 2011, 13, 2626-2629.

DOI: 10.1021/ol200740r (free Supporting Information)


see article for more reactions

Abstract

A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with a broad range of sulfonamides in a reductive bond cleaving pathway to provide the corresponding amines, hydrocarbons and thiols. The reagent could also cleave sulfonates to the corresponding alcohols.


see article for more examples



Key Words

Amines, Toluenesulfonamides, Titanium (low valent), Magnesium


ID: J54-Y2011-1490