HFIP-Promoted Friedel–CraftsAllenylation ofImidazopyridines with Propargyl Alcohols at Room Temperature

Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo­[1,2-<i>a</i>]­pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In this method, HFIP, besides offering hydrogen bonding with propargyl alcohol, also stabilizes the resultant carbocation, thus forming the product. This method also enables the straightforward synthesis of 1,3-enynes. The current method offers a large substrate diversity with good to excellent yields. We also demonstrated gram-scale synthesis and synthetic modifications.

Publication Details

Journal
Figshare
Published
2025-03-26
DOI
https://doi.org/10.1021/acs.joc.5c00326.s001
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

HFIP-Promoted Friedel–CraftsAllenylation ofImidazopyridines with Propargyl Alcohols at Room Temperature

Figshare
Catalytic Alkyne Reactions
article

HFIP-Promoted Friedel–CraftsAllenylation ofImidazopyridines with Propargyl Alcohols at Room Temperature

article en

Abstract

Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo­[1,2-<i>a</i>]­pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In this method, HFIP, besides offering hydrogen bonding with propargyl alcohol, also stabilizes the resultant carbocation, thus forming the product. This method also enables the straightforward synthesis of 1,3-enynes. The current method offers a large substrate diversity with good to excellent yields. We also demonstrated gram-scale synthesis and synthetic modifications.

Figshare
Openalex Percentile: Top 69%
Catalytic Alkyne Reactions
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HFIP-Promoted Friedel–CraftsAllenylation ofImidazopyridines with Propargyl Alcohols at Room Temperature · Figshare (2025) | TGRS Research Map | TGRS