Palladium Membrane-Installed Microchannel Devices for Instantaneous Suzuki-Miyaura Cross-Coupling

Instantaneous catalytic carbon-carbon bond-forming reactions were achieved in catalytic membrane-installed microchannel devices that have a polymeric palladium-complex membrane. The catalytic membrane-installed microchannel devices were provided inside the microchannels by means of coordinative and ionic molecular convolution at the interface between the organic and aqueous phases flowing laminarly, in which both non-crosslinked linear polymer ligands and palladium species dissolved. The palladium-catalyzed Suzuki-Miyaura reaction of aryl, heteroaryl, and alkenyl halides with arylboronic acids and sodium tetraarylborates was performed with the catalytic membrane-installed microchannel devices to give quantitative yields of biaryls, heterobiaryls, and aryl alkenes within 5 s of residence time in the defined channel region. These microchannel devices were applied to the instantaneous allylic arylation reaction of allylic esters with arylboron reagents under microflow conditions to afford the corresponding coupling products within 1 s of residence time.