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Synthesis 2024; 56(10): 1601-1607
DOI: 10.1055/a-2256-9837
paper

I2-Catalyzed Oxidative Acylation of Tertiary Amines via C–N Bond Cleavage

Xin Ge
a   State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830017, P. R. of China
,
Ping Lei
a   State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830017, P. R. of China
,
Qin Su
a   State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830017, P. R. of China
,
Ying-Ming Pan
b   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Gui Lin, 541004, P. R. of China
,
Keyume Ablajan  ∗
a   State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830017, P. R. of China
b   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Gui Lin, 541004, P. R. of China
› InstitutsangabenThe authors are grateful for financial support from the State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources through Guangxi Normal University (Grant No. CMEMR 2020-B12) and the National Natural Science Foundation of China (Grant No. 21961038).
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Abstract

The development of catalysts for the amidation of tertiary amines with acyl chlorides through oxidative C–N bond cleavage is rather challenging. By employing iodine as the catalyst, a broad range of aromatic acyl chlorides and tertiary amines are efficiently converted into amides in good yields under mild conditions. A plausible mechanistic pathway is proposed for this transformation and is supported by appropriate control experiments.

Key words

amidation - I2 catalysis - C–N cleavage - acyl chloride - tertiary amine

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2256-9837.
  • Supporting Information


Publikationsverlauf

Eingereicht: 12. November 2023

Angenommen nach Revision: 30. Januar 2024

Accepted Manuscript online:
30. Januar 2024

Artikel online veröffentlicht:
14. Februar 2024

© 2024. Thieme. All rights reserved

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