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Título
Problematic ArF–Alkynyl coupling with fluorinated aryls. From partial success with alkynyl stannanes to efficient solutions via mechanistic understanding of the hidden complexity
Autor
Año del Documento
2022
Editorial
American Chemical Society
Descripción
Producción Científica
Documento Fuente
Journal of the American Chemical Society, 2023, vol.145, n. 1, p. 527–536
Abstract
The synthesis of aryl–alkynyl compounds is usually achieved via Sonogashira catalysis, but this is inefficient for fluorinated aryls. An alternative method reported by Shirakawa and Hiyama, using alkynylstannanes and hemilabile PN ligands, works apparently fine for conventional aryls, but it is also poor for fluorinated aryls. The revision of the unusual literature cycle reveals the existence and nature of unreported byproducts and uncovers coexisting cycles and other aspects that explain the reasons for the conflict. This knowledge provides a full understanding of the real complexity of these aryl/alkynylstannane systems and the deviations of their evolution from that of a classic Stille process, providing the clues to design several very efficient alternatives for the catalytic synthesis of the desired ArF–alkynyl compounds in almost quantitative yield. The same protocols are also very efficient for the catalytic synthesis of alkynyl–alkynyl’ hetero- and homocoupling.
Materias Unesco
23 Química
Palabras Clave
Catalysis
Catálisis
Palladium
Paladio
ISSN
0002-7863
Revisión por pares
SI
Patrocinador
Ministerio de Asuntos Económicos y Transformación Digital (project PID2020- 118547GB-I00)
Junta de Castilla y León (project VA224P20)
Irish Research Council (GOIPD/2020/701)
Universidad de Valladolid (Margarita Salas program, ref. CONVREC- 2021-221)
Junta de Castilla y León (project VA224P20)
Irish Research Council (GOIPD/2020/701)
Universidad de Valladolid (Margarita Salas program, ref. CONVREC- 2021-221)
Version del Editor
Propietario de los Derechos
© 2022 The Authors
Idioma
eng
Tipo de versión
info:eu-repo/semantics/publishedVersion
Derechos
openAccess
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