op9b00196_si_001.pdf (2.78 MB)
Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System
journal contribution
posted on 2019-06-17, 14:39 authored by Gregory
L. Beutner, John R. Coombs, Rebecca A. Green, Bahar Inankur, Dong Lin, Jun Qiu, Frederick Roberts, Eric M. Simmons, Steven R. WisniewskiThe
palladium-catalyzed coupling of aryl and heteroaryl chlorides
with primary amides under mild homogeneous reaction conditions is
reported. Successful C–N coupling is enabled by the use of
a unique “dual-base” system consisting of DBU and NaTFA,
which serve as proton acceptor and halide scavenger, respectively,
using low catalyst loadings (0.5 mol %) with readily available, air-stable
palladium precatalysts. The DBU/NaTFA system also enables the room-temperature
coupling of primary aryl amines with aryl chlorides and is tolerant
of a variety of base-sensitive functional groups.
