Bioinspired zinc-mediated umpolung thiolation of alkyl electrophiles: reaction development, scope and mechanism

Xu, Yuenian; Zhang, Yan; Liu, Yong; Sun, Wen-Wu; Huang, Jie; He, Hui; Wu, Yingjie; Liu, Wen; Ni, Shao-Fei; Xiao, Xu-Qiong; Shao, Xinxin

doi:10.1007/s11426-023-1795-9

Cited by 5 publications

(2 citation statements)

References 65 publications

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“…20 Meanwhile, our group discovered that Zn played a unique role in the activation of electrophilic thiolating reagents to generate a nucleophilic zinc thiolate, which could thiolate a series of alkyl electophiles. 21 Based on these critical findings, we wondered whether a nickel catalysis-free thiolation could be achieved if nucleophilic zinc thiolate was formed directly from the insertion of a S–S bond in redox-active thiosulfonates. Herein, we illustrated an easy-to-handle, scalable and practical protocol via Zn-mediated umpolung thiolation of alkyl halides with thiosulfonates to construct various C(sp 3 )–S bonds under redox-neutral conditions (Scheme 1D).…”

Section: Introductionmentioning

confidence: 99%

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Fan,

Zhao,

Liang

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Fan,

Zhao,

Liang

et al. 2024

Org. Chem. Front.

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“…Compared with ynamides and haloalkynes, research on alkynyl sulfides has been relatively underdeveloped . Thus, it is highly desired to develop a novel reaction model to synthesize sulfur-containing compounds from alkynyl sulfides …”

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confidence: 99%

Lewis Acid-Catalyzed Formal [4 + 2] Reaction of Alkynyl Sulfides and 2-Pyrones To Access Polysubstituted Aryl Sulfides

Huang,

Xing,

Jiang

et al. 2024

J. Org. Chem.

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A practical and efficient method to access polysubstituted aryl sulfides has been discovered via a Lewis acid-catalyzed reaction between alkynyl sulfide and 2-pyrone, involving a Diels−Alder/retro-Diels−Alder pathway. Alkynyl sulfide as an electron-rich dienophile and 2-pyrones as electronpoor dienes are conjunctively transformed into a series of polysubstituted aryl sulfides with broad functional group compatibility in good to excellent yields (40 examples, 43−88% yield). The robustness and practicality of the protocol has been demonstrated through gram-scale synthesis and the ease of transformation of the resulting products.

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Bis(phenylsulfonyl)sulfide as a Bifunctional Single‐Sulfur Source for the Rapid Assembly of Unsymmetric Diaryl Sulfides Enabled by Copper Catalyst

Wang,

Zhou,

Huang

et al. 2024

ChemistrySelect

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Rapid access to unsymmetrical diaryl sulfides through a bifunctional single‐sulfur source is a very attractive strategy. Here we report the utilization of bis(phenylsulfonyl)sulfide as a bielectrophilic sulfide platform molecule for chemoselective and sequential installation of two different aryl nucleophiles by twice copper‐catalyzed Chan–Lam‐type cross couplings to access diverse unsymmetrical diaryl sulfides. This strategy demonstrates good tolerance to a wide range of aryl boronic acids under different metal catalysts, good functional group compatibility, as well as the extension to the modification of complex bioactive molecules.

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Bioinspired zinc-mediated umpolung thiolation of alkyl electrophiles: reaction development, scope and mechanism

Cited by 5 publications

References 65 publications

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Nickel-free cross-electrophile coupling of unactivated alkyl bromides with thiosulfonates and sulfinyl sulfones

Lewis Acid-Catalyzed Formal [4 + 2] Reaction of Alkynyl Sulfides and 2-Pyrones To Access Polysubstituted Aryl Sulfides

Bis(phenylsulfonyl)sulfide as a Bifunctional Single‐Sulfur Source for the Rapid Assembly of Unsymmetric Diaryl Sulfides Enabled by Copper Catalyst

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