A Strategy for the Formal C-N Cross-Coupling of Tertiary Amines.

Autor: Ledwith PR; Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD., Cooney ML; Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD.; School of Chemistry, University of Bristol, Cantock's Close, Bristol, United Kingdom, BS8 1TS., Bahou KA; Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD., García-Cárceles J; School of Chemistry, University of Bristol, Cantock's Close, Bristol, United Kingdom, BS8 1TS., Thomson J; School of Chemistry, University of Bristol, Cantock's Close, Bristol, United Kingdom, BS8 1TS., Bower JF; Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 09; Vol. 63 (50), pp. e202411555. Date of Electronic Publication: 2024 Oct 22.
DOI: 10.1002/anie.202411555
Abstrakt: We report a strategy for the formal C-N cross-coupling of tertiary amines via the in situ generation and displacement of N-acyl ammonium species. Specifically, treatment of diverse tertiary amines with TFAA or chloroformates in the presence of NaI leads to the efficient generation of alkyl iodides, which can be engaged directly in Ni-catalyzed cross-couplings. The protocol is applicable to acyclic and cyclic systems, including highly hindered variants. Applications to the late-stage modification of complex heterocycles are presented.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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