Metal‐Free Tunable 1,2‐Difunctionalization of Terminal Alkynes: Synthesis of β‐Substituted α,β‐Unsaturated Ketones

A metal‐free tunable 1,2‐difunctionalization of the terminal alkynes showcasing a tandem installation of C−C and C−S bonds has been developed. The key enabling factor for the approach is the use of acetic acid as an acyl source to synthesize β‐substituted α,β‐unsaturated ketones. The reaction at roo...

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Bibliographic Details
Published in:Chemistry : a European journal 2023-12, Vol.29 (67), p.e202302294-n/a
Main Authors: Bhat, Muneer‐Ul‐Shafi, Ganie, Majid Ahmad, Shah, Bhahwal Ali
Format: Article
Language:English
Subjects:
Acetic acid
acid
Acylation
alkyne
Alkynes
Carbon
Chemistry
Ketones
Room temperature
Substitutes
thiophenol
triflic anhydride
α,β-unsaturated ketones
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Summary:A metal‐free tunable 1,2‐difunctionalization of the terminal alkynes showcasing a tandem installation of C−C and C−S bonds has been developed. The key enabling factor for the approach is the use of acetic acid as an acyl source to synthesize β‐substituted α,β‐unsaturated ketones. The reaction at room temperature leads to the regioselective acylation at the terminal carbon of alkynes, whereas at −78 °C, the acylation occurs at the more substituted carbon. A new method efficiently adds C−C and C−S bonds to terminal alkynes, allowing for accessing a range of β‐substituted α,β‐unsaturated ketones. The versatility of the approach lies in its ability to tune the reaction conditions to target different positions of the alkyne by switching temperature.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302294