Affiliation:
1. Interdisciplinary Research Center for Catalytic Chemistry National Institute of Advanced Science and Technology (AIST) 1-1-1 Higashi Tsukuba Ibaraki 305-8565 Japan
2. Tokyo Institute of Technology School of Materials and Chemical Technology 2-12-1 Ookayama Meguro-ku Tokyo 152-8552 Japan
3. Toyota Central R&D Labs., Inc. Nagakute Aichi 480-1192 Japan
Abstract
AbstractPhosphine periodic mesoporous organosilicas (R‐P‐PMO‐TMS: R=Ph, tBu), which possess electron‐donating alkyl substituents on the phosphorus atom, were synthesized using bifunctional compounds with alkoxysilyl‐ and phosphino groups, bis[3‐(triethoxysilyl)propyl]phenylphosphine borane (1 a) and bis[3‐(triethoxysilyl)propyl]‐tert‐butylphosphine borane (1 b). Immobilization of Pd(0) species was performed to give R‐P‐Pd‐PMO‐TMS: R=Ph (2 a), tBu (3 a), respectively. The Pd(0) immobilized 2 a and 3 a were applicable as catalysts for Suzuki‐Miyaura cross‐coupling reactions of aryl chlorides with phenylboronic acid. It was revealed that 3 a bearing more electron‐donating tBu groups exhibited higher catalytic activity. Various functional groups including both electron withdrawing and donating substituents were compatible in the system. The recyclability of 3 a was examined to support its moderate utility for the recycle use.
Subject
General Chemistry,Catalysis,Organic Chemistry