Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 24, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202202794
Keywords
Acyl Iodides; Amides; Cooperative Catalysis; N-C(O) Activation; Transamidation
Categories
Funding
- National Nature and Science Foundation of China [21871070]
- Key RAMP
- D project of Hainan province [ZDYF2020168]
- Rutgers University
- NSF CAREER [CHE-1650766]
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The challenging transamidation of unactivated tertiary amides has been accomplished via cooperative acid/iodide catalysis. This method provides a direct route to amide-to-amide bond interconversion with excellent chemoselectivity using equivalent amounts of amines. The combination of acid and iodide activates the amide C-N bond through electrophilic catalytic activation, enabling the production of new desired transamidated products with wide substrate scope.
The challenging transamidation of unactivated tertiary amides has been accomplished via cooperative acid/iodide catalysis. Most crucially, the method provides a novel manifold to re-route the reactivity of unactivated N,N-dialkyl amides through reactive acyl iodide intermediates, thus reverting the classical order of reactivity of carboxylic acid derivatives. This method provides a direct route to amide-to-amide bond interconversion with excellent chemoselectivity using equivalent amounts of amines. The combination of acid and iodide has been identified as the essential factor to activate the amide C-N bond through electrophilic catalytic activation, enabling the production of new desired transamidated products with wide substrate scope of both unactivated amides and amines, including late-stage functionalization of complex APIs (>80 examples). We anticipate that this powerful activation mode of unactivated amide bonds will find broad-ranging applications in chemical synthesis.
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