Synlett 2014; 25(13): 1869-1872
DOI: 10.1055/s-0034-1378315
letter
© Georg Thieme Verlag Stuttgart · New York

Molybdenum-Mediated Desulfurization of Thiols and Disulfides

Zhen Wang
a   Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Email: kuninobu@mol.f.u-tokyo.ac.jp   Email: kanai@mol.f.u-tokyo.ac.jp
b   ERATO, Japan Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Fax: +81(3)56845206
,
Yoichiro Kuninobu*
a   Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Email: kuninobu@mol.f.u-tokyo.ac.jp   Email: kanai@mol.f.u-tokyo.ac.jp
b   ERATO, Japan Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Fax: +81(3)56845206
,
Motomu Kanai*
a   Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Email: kuninobu@mol.f.u-tokyo.ac.jp   Email: kanai@mol.f.u-tokyo.ac.jp
b   ERATO, Japan Science and Technology Agency (JST), Kanai Life Science Catalysis Project, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Fax: +81(3)56845206
› Author Affiliations
Further Information

Publication History

Received: 11 April 2014

Accepted after revision: 13 May 2014

Publication Date:
06 June 2014 (online)


Abstract

We have successfully achieved the molybdenum hexacarbonyl [Mo(CO)6] mediated desulfurization of thiols and disulfides. In this reaction, the sulfhydryl (SH) mercapto groups of aryl, benzyl, primary and secondary alkyl thiols, and S–S single bonds of disulfides can be removed. This reaction has high functional group tolerance and is not affected by steric hindrance. The results of the reactions in acetone-d 6 suggest that the sources of hydrogen in the thiol and disulfide desulfurizations are the hydrogen atom(s) of a sulfhydryl group and acetone (solvent), respectively, and that the desulfurization proceeds via the formation of an organomolybdenum species.

Supporting Information