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Open AccessFeature PaperArticle

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

1
Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
2
Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Kouki Matsubara
Molecules 2019, 24(9), 1671; https://doi.org/10.3390/molecules24091671
Received: 11 April 2019 / Revised: 26 April 2019 / Accepted: 26 April 2019 / Published: 28 April 2019
(This article belongs to the Special Issue Nickel Complexes for Catalysis)
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. View Full-Text
Keywords: nickel; acyl fluorides; stannylation; decarbonylation; carbon-tin bond formation nickel; acyl fluorides; stannylation; decarbonylation; carbon-tin bond formation
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MDPI and ACS Style

Wang, X.; Wang, Z.; Liu, L.; Asanuma, Y.; Nishihara, Y. Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions. Molecules 2019, 24, 1671.

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