Trifluoromethanesulfonic Acid‐Promoted Esterification of Unactivated Tertiary Amides with Tetrahydrofurans and Potassium Halides to Access Haloalkyl Esters

Abstract Herein, we report a trifluoromethanesulfonic acid‐promoted esterification reaction of unactivated N,N ‐dialkyl amides with tetrahydrofurans and potassium halides. One‐pot construction of carbon‐halogen and carbon‐oxygen bonds was achieved under transition‐metal‐free condition to furnish a wide range of haloalkyl esters in 22 – 82% yields. Preliminary mechanistic studies imply that this esterification possibly proceeds through the cross‐coupling of in situ generated acyl halides and 4‐halobutanols.

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Journal
ChemistrySelect
Published
2025-11-01
DOI
https://doi.org/10.1002/slct.202505934
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Trifluoromethanesulfonic Acid‐Promoted Esterification of Unactivated Tertiary Amides with Tetrahydrofurans and Potassium Halides to Access Haloalkyl Esters

Yueyue Fan, Dahee Song, Yongbing Liu, Fangfang Feng
ChemistrySelect
Advanced Synthetic Organic Chemistry
article

Trifluoromethanesulfonic Acid‐Promoted Esterification of Unactivated Tertiary Amides with Tetrahydrofurans and Potassium Halides to Access Haloalkyl Esters

Yueyue Fan, Dahee Song, Yongbing Liu, Fangfang Feng
article en

Abstract

Abstract Herein, we report a trifluoromethanesulfonic acid‐promoted esterification reaction of unactivated N,N ‐dialkyl amides with tetrahydrofurans and potassium halides. One‐pot construction of carbon‐halogen and carbon‐oxygen bonds was achieved under transition‐metal‐free condition to furnish a wide range of haloalkyl esters in 22 – 82% yields. Preliminary mechanistic studies imply that this esterification possibly proceeds through the cross‐coupling of in situ generated acyl halides and 4‐halobutanols.

ChemistrySelectVol. 10(43)
Zero to Three (US), Hebei Normal University (CN)
Hebei Normal University, Natural Science Foundation of Hebei Province, Chinese University of Hong Kong
Openalex Percentile: Top 74%
Advanced Synthetic Organic Chemistry
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