Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes

Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions: Q. Chen, L. Fu, J. You, Y. Nishihara

Synlett 2021, 32, DOI: 10.1055/s-0040-1705954


Acyl fluorides – which can be efficiently and readily prepared from the corresponding carboxylic acids – are considerably more stable than their chloride counterparts; still, they display high reactivity and can very effectively function as acyl cation synthons in a range of transformations, including metal-catalyzed cross-coupling reactions. Recently, the group of Professor Yasushi Nishihara from Okayama University (Japan) reported a novel transformation which can be used to prepare a variety of aryl alkynes from the corresponding acyl fluorides.

Professor Nishihara said: “Nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes has been realized under copper-free conditions. This new synthetic route of internal silylethynes exhibited a wide range of substrate scope. The undesired formation of homo-coupled products and conjugate enones was efficiently retarded.”

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