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Synlett 2021; 32(15): 1560-1564
DOI: 10.1055/s-0040-1705954
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Modern Nickel-Catalyzed Reactions

Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions

Qiang Chen
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
,
Liyan Fu
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
,
Jingwen You
a   Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan
,
Yasushi Nishihara  ∗
b   Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan   Email: ynishiha@okayama-u.ac.jp
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Abstract

Nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes under copper-free conditions is described. This newly developed method has a wide substrate scope, affording internal silylethynes in moderate to high yields. The formation of 1,3-diynes as homocoupled products and conjugate enones as carbonyl-retentive products were effectively suppressed.

Key words

nickel catalysis - decarbonylation - silylalkynes - alkynylation - acyl fluorides - sila-Sonogashira–Hagihara reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705954.
  • Supporting Information


Publication History

Received: 09 September 2020

Accepted after revision: 21 September 2020

Article published online:
28 October 2020

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