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. 2019 Apr 28;24(9):1671.
doi: 10.3390/molecules24091671.

Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions

Xiu Wang  1 , Zhenhua Wang  2 , Li Liu  3 , Yuya Asanuma  4 , Yasushi Nishihara  5
Affiliations

Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions

Xiu Wang et al. Molecules. .

Abstract

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.

Keywords: acyl fluorides; carbon-tin bond formation; decarbonylation; nickel; stannylation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Various synthetic routes for arylstannanes.
Scheme 2
Scheme 2
One-pot reaction of decarbonylative stannylation/Migita-Kosugi-Stille reaction of 1a.
Scheme 3
Scheme 3
Proposed mechanism.
See this image and copyright information in PMC

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