Suzuki-Miyaura Cross-Coupling Reaction Using Palladium Catalysts Supported on Phosphine Periodic Mesoporous Organosilica

Kosuke Iizuka; Yoshifumi Maegawa; Yoshihiro Shimoyama; Kei Sakamoto; Natsuko Kayakiri; Yasutomo Goto; Yuki Naganawa; Shinji Tanaka; Masaru Yoshida; Shinji Inagaki; Yumiko Nakajima

doi:10.1002/chem.202303159

Suzuki-Miyaura Cross-Coupling Reaction Using Palladium Catalysts Supported on Phosphine Periodic Mesoporous Organosilica

Chemistry. 2024 Feb 7;30(8):e202303159. doi: 10.1002/chem.202303159. Epub 2023 Dec 14.

Authors

Affiliations

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.

PMID: 38018377
DOI: 10.1002/chem.202303159

Abstract

Phosphine 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.

Keywords: Suzuki-Miyaura cross-coupling; mesoporous organosilica; phosphorus ligand.