Rhodium-catalyzed methylthio transfer reaction between ketone alpha-positions: reversible single-bond metathesis of C-S and C-H bonds

Organic Letters
Mieko ArisawaMasahiko Yamaguchi

Abstract

In the presence of a catalytic amount of RhH(PPh(3))(4) and 1,2-bis(diphenylposphino)ethane (dppe), alpha-phenylthio ketones were methylthiolated with p-cyano-alpha-methylthioacetophenone giving alpha-phenylthio-alpha-methylthio ketones. The methylthio transfer reaction between the ketone alpha-positions was reversible and at equilibrium, and the methylthio group was transferred in preference to the phenylthio group. The reaction of tertiary alkyl methylthiomethyl ketones proceeded in high yields; the reaction of diastereomeric 4-(tert-butyl)-2-phenylthiocyclohexanones gave an axial 2-methylthiolated product.

References

Mar 14, 2003·Organic Letters·Masahiro Egi, Lanny S Liebeskind

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Citations

Oct 12, 2010·Chemical & Pharmaceutical Bulletin·Mieko ArisawaMasahiko Yamaguchi
Sep 16, 2014·International Journal of Oral and Maxillofacial Surgery·N AbeE Tanaka
Oct 14, 2014·Chemical Society Reviews·Chao ShenXiaogang Liu
Aug 14, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mieko Arisawa, Masahiko Yamaguchi
Sep 20, 2019·The Journal of Organic Chemistry·Issei SuzukiFumitoshi Kakiuchi

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