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

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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.

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Key Words

Amines, Toluenesulfonamides, Titanium (low valent), Magnesium

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ID: J54-Y2011-1490