Molybdenum-Mediated Desulfurization of Thiols and Disulfides

Zhen Wang; Yoichiro Kuninobu; Motomu Kanai

doi:10.1055/s-0034-1378315

Synlett, Table of Contents

Synlett 2014; 25(13): 1869-1872
DOI: 10.1055/s-0034-1378315

letter

Molybdenum-Mediated Desulfurization of Thiols and Disulfides

Zhen Wang

^aGraduate 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

^bERATO, 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*

^aGraduate 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

^bERATO, 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*

^aGraduate 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

^bERATO, 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

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Abstract

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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.

Key words

desulfurization - molybdenum - thiols - disulfides - cleavage

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References

References and Notes

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