Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides

Cheng Ye; Weiqi Tong; Fan Wu

doi:10.1055/s-0040-1719881

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(09): 2251-2257
DOI: 10.1055/s-0040-1719881

paper

Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides

Cheng Ye

^aSchool of Materials Science and Engineering, Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China

,

Weiqi Tong

^aSchool of Materials Science and Engineering, Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China

,

Fan Wu∗

^bInstitute of Drug Discovery Technology and Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

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Abstract

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Abstract

A nickel-catalyzed cross-electrophile coupling is disclosed in which a range of vinyl bromides were utilized as electrophiles with oxalates derived from α-hydroxy carbonyls as precursors to carbonyl radical coupling partners. This method is compatible with a broad range of functional groups, providing a complementary solution for the construction of β,γ-unsaturated carbonyl compounds.

Key words

nickel catalysis - cross-electrophile coupling - vinylation - oxalates - radicals

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15 A preliminary study showed that the oxalate derivative of an α-hydroxy amide was also a viable substrate. For details of this reaction, see the Supporting Information.

Zusatzmaterial

Supporting Information