Cargando…

Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides

Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C–C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp(2), and sp(3)) with aromatic (pseudo) halides (sp(2)). Here we...

Descripción completa

Detalles Bibliográficos
Autores principales: Mondal, Anirban, Visser, Paco, Doze, Anna M., Buter, Jeffrey, Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8320736/
https://www.ncbi.nlm.nih.gov/pubmed/34236070
http://dx.doi.org/10.1039/d1cc02762j
Descripción
Sumario:Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C–C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp(2), and sp(3)) with aromatic (pseudo) halides (sp(2)). Here we present an efficient method for the cross-coupling of benzyl bromides (sp(3)) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.