RT info:eu-repo/semantics/article
T1 Problematic ArF–Alkynyl coupling with fluorinated aryls. From partial success with alkynyl stannanes to efficient solutions via mechanistic understanding of the hidden complexity
A1 Marcos Ayuso, Guillermo
A1 Peñas de Frutos, Marconi Nicolás
A1 Gallego Díaz, Ana María
A1 García Melchor, Max
A1 Martínez de Ilarduya Martínez de Ilarduya, Jesús María
A1 Espinet Rubio, Pablo
K1 Catalysis
K1 Catálisis
K1 Palladium
K1 Paladio
K1 23 Química
AB 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.
PB American Chemical Society
SN 0002-7863
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/57926
UL https://uvadoc.uva.es/handle/10324/57926
LA eng
NO Journal of the American Chemical Society, 2023, vol.145, n. 1, p. 527–536
NO Producción Científica
DS UVaDOC
RD 23-may-2024