Metal-free base-promoted sulfenylation for the synthesis of α-arylthio-α,β-unsaturated ketones

A new sulfenylation reaction has been established, stereoselectively affording 37 examples of α-arylthio-α,β-unsaturated ketones with generally good yields via a metal-free three-component reaction of α-thiocyanate ketones with diaryliodonium salts and 1,2-dicarbonyls. The reaction enabled multiple...

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Bibliographic Details
Published in:Tetrahedron 2018-02, Vol.74 (5), p.585-593
Main Authors: Zhu, Xiao-Tong, Zhao, Qi, Wang, Shi-Da, Zhang, Tian-Shu, Cai, Pei-Jun, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Stereoselectivity
Sulfenylation
Three-component reaction
α-arylthio-α,β-unsaturated ketones
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Summary:A new sulfenylation reaction has been established, stereoselectively affording 37 examples of α-arylthio-α,β-unsaturated ketones with generally good yields via a metal-free three-component reaction of α-thiocyanate ketones with diaryliodonium salts and 1,2-dicarbonyls. The reaction enabled multiple bond-forming events including C(sp2)–S formation to provide a high-efficient and practical method toward α-arylthio-α,β-unsaturated ketones. The reasonable mechanism for forming α-arylthio-α,β-unsaturated ketones was proposed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.12.037