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Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

2-(Trifluoromethylthio)benzothiazolium triflate (BT-SCF₃) was used as deoxyfluorinating reagent for the synthesis of versatile acyl fluorides directly from the corresponding carboxylic acids. These acyl fluorides were reacted with amines in a one-pot protocol to form different amides, including dipeptides, under mild and operationally simple conditions in high yields. Mechanistic studies suggest that BT-SCF₃ can generate acyl fluorides from carboxylic acids via two distinct pathways, which allows the deoxyfluorinating reagent to be employed in sub-stoichiometric amounts.

Publication metadata

Author(s): Mass LM, Haswell A, Hughes R, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Beilstein Journal of Organic Chemistry

Year: 2024

Volume: 20

Pages: 921–930

Online publication date: 23/04/2024

Acceptance date: 05/04/2024

Date deposited: 24/04/2024

ISSN (print): 2195-951X

ISSN (electronic): 1860-5397

Publisher: Beilstein-Institut

URL: https://doi.org/10.3762/bjoc.20.82

DOI: 10.3762/bjoc.20.82

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