Efficient Suzuki coupling of aryl chlorides catalyzed by palladium(0) with a P,N heteroligand and isolation of unsaturated intermediates

Abstract

A mixture of Pd2(dba)3/[η-C5H 4CH=N(C6H5)]Fe[η-C5H 4P(t-Bu)2] (1) efficiently catalyzes the Suzuki cross-couplings of a range of arylboronic acids and aryl chlorides, affording the desired biaryl products in high isolated yields. Two catalytically active Pd(0) intermediates, viz. 16-electron [η-C5H4CH-N(C6H 5)]Fe[η-C5H4P-(t-Bu)2]Pd(dba) (2) and 14-electron linear Pd{[η-C5H4CH=N(C 6H5)]Fe[η-C5H4P-(t-Bu) 2]}2 (3) together with an oxidative addition product are isolated and crystallo-graphically established.