Simple, general, and efficient synthesis of meso-substituted borondipyrromethenes from a single platform.
An unprecedented synthesis of 8-substituted-borondipyrromethenes is described starting from 8-thiomethylbodipy 1. Aryl, heteroaryl, alkenyl, and organometallic boronic acids smoothly reacted with 1 in the presence of a catalytic amount of Pd(0) and a stoichiometric amount of Cu(I)-2-thienylcarboxylate under neutral conditions to give the corresponding Bodipy analogues in good to quantitative yields (20 examples). A remarkable reactivity was observed in some cases, e.g., ferrocenylboronic acid gave the product in 98% isolated yield after only 10 min at 55 degrees C.
Peña-Cabrera
Eduardo
E
Departamento de Química, Universidad de Guanajuato, Col. Noria Alta S/N, Guanajuato, Gto. 36050, Mexico. eduardop@quijote.ugto.mx
Aguilar-Aguilar
Angélica
A
Gonzalez-Domínguez
Martha
M
Lager
Erik
E
Zamudio-Vazquez
Rubí
R
Godoy-Vargas
Jazmín
J
Villanueva-García
Fabian
F