Synlett 2024; 35(07): 807-810
DOI: 10.1055/a-2159-4369
letter

Nickel-Catalyzed Decarbonylation of α-Oxyacetic Acid Thioesters: Hydroxymethylation of Mercaptans

Rui Tian
,
Jia-Xin Li
,
Yong-Ming Zhu


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Abstract

A strategy for the Ni-catalyzed decarbonylation of α-oxyacetic acid thioesters is described, providing a new pathway for the synthesis of monosulfide acetals, and further proving that oxygen atoms can stabilize an α-carbocation and promote a decarbonylation reaction. This method has good functional-group compatibility and can tolerate a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents. In addition, this method complements the conventional cross-coupling reactions.

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Publication History

Received: 25 June 2023

Accepted after revision: 23 August 2023

Accepted Manuscript online:
23 August 2023

Article published online:
11 October 2023

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