Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents

Han Wang; Duo Zhang; Mengwei Cao; Carsten Bolm

doi:10.1055/s-0037-1610369

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CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 271-275
DOI: 10.1055/s-0037-1610369

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Electrophilic Sulfoximidations of Thiols by Hypervalent Iodine Reagents

Han Wang

,

Duo Zhang

,

Mengwei Cao

,

Carsten Bolm *

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: Carsten.bolm@rwth-aachen.de

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Abstract

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Abstract

A new electrophilic sulfoximidation of thiols has been developed. Using sodium hydride as a base, the treatment of sulfoximidoyl-containing hypervalent iodine(III) reagents with thiols affords the corresponding N-sulfenylsulfoximines (N-thiosulfoximines) in good to excellent yields. A plausible mechanism is proposed.

Key words

sulfoximidation - thiol - N-sulfenylsulfoximine - hypervalent iodine reagents - ligand exchange

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References

References

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