Exploring the reactivity of (hetero)aryl amides in the Chan‐Evans‐Lam reaction with arylalkenyl boron reagents
Abstract The unique reactivity and stability of enamides make them attractive reagents in organic synthesis. Herein, we investigated the reactivity of acetanilides and pyridyl acetamides in the formation of a C−N bond through a Chan‐Evans‐Lam reaction using arylalkenyl boron‐based reagents yielding a wide scope of N ‐aryl enamides with an E configuration. The products obtained have been applied in the synthesis of N ‐heterocycles, an important scaffold in several biologically active compounds, via sequential Heck reaction to prove the practical utility of the prepared N ‐aryl enamides.
Authors
- Fábio M. F. Santos (ORCID: https://orcid.org/0000-0002-9057-9276)
- Samuel Guieu (ORCID: https://orcid.org/0000-0002-7439-209X)
- M. Manuel B. Marques
- Joana R. M. Ferreira (ORCID: https://orcid.org/0000-0003-0995-8680)
- Bruna F. L. Guerreiro
Institutions
- University of Lisbon (PT)
- Rede de Química e Tecnologia (PT)
- University of Aveiro (PT)
- Universidade Nova de Lisboa (PT)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-11-18
- DOI
- https://doi.org/10.1002/ejoc.202400805
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Universidade de Aveiro
- Ministerio de Economía y Competitividad
- Universidade de Lisboa
- Ministério da Ciência, Tecnologia e Ensino Superior
- Programa Operacional Regional do Centro
- Laboratório Associado para a Química Verde
- Centro de Investigação em Materiais Cerâmicos e Compósitos
- Fundação para a Ciência e a Tecnologia