Tetrahedron

Rhodium-catalyzed α-methylthiolation reaction of unactivated ketones using 1, 2-diphenyl-2-methylthio-1-ethanone for the methylthio transfer reagent

M Arisawa, F Toriyama, M Yamaguchi

Index: Arisawa, Mieko; Toriyama, Fumihiko; Yamaguchi, Masahiko Tetrahedron, 2011 , vol. 67, # 12 p. 2305 - 2312

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Citation Number: 9

Abstract

In the presence of catalytic amounts of RhH (PPh3) 4, 1, 2-bis (diphenylphosphino) ethane (dppe), and dimethyl disulfide, ketones without α-activating groups were α-methylthiolated with 1, 2-diphenyl-2-methylthio-1-ethanone giving α-methylthio ketones. The reaction of unsymmetrical ketones proceeded at the more substituted carbons. The initial formation of kinetic α-methylthiolated products followed by their rearrangement to thermodynamic ...