Issue 11, 2022

The bulky Pd-PEPPSI-embedded conjugated microporous polymer-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides and arylboronic acids

Abstract

Through a post-synthesis method, a type of bulky N-heterocyclic carbene (NHC) functionalized conjugated microporous polymer supporting a palladium-based molecular catalyst has been developed. The resulting heterogeneous catalyst Pd-PEPPSI-CMP, showing greater steric hindrance around the palladium center than a monomer Pd-PEPPSI-IPr catalyst, demonstrated much higher catalytic efficiency for Suzuki–Miyaura cross-coupling reactions of aryl chlorides under aerobic conditions. The superior utility of Pd-PEPPSI-CMP in catalysis was elucidated through the broad substrate scope (30 examples, 76–98% yields), the tolerance for a variety of functional groups, the excellent recyclability (15 cycles), and an example of gram-scale synthesis (10 mmol). Moreover, its utility has been highlighted via the synthesis of a bioactive molecule (boscalid) and the direct late-stage functionalization of pharmaceuticals (4 examples, 76–85% yields). These results demonstrated that Pd-PEPPSI-CMP could be used as an efficient and robust heterogeneous catalyst with potential industrial applications.

Graphical abstract: The bulky Pd-PEPPSI-embedded conjugated microporous polymer-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides and arylboronic acids

Supplementary files

Article information

Article type
Paper
Submitted
04 Dec 2021
Accepted
07 Feb 2022
First published
11 Feb 2022

Polym. Chem., 2022,13, 1547-1558

The bulky Pd-PEPPSI-embedded conjugated microporous polymer-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides and arylboronic acids

C. Wang, W. Zhao, Y. Li, Y. Han, J. Zhang, Q. Li, K. Nie, J. Chang and F. Liu, Polym. Chem., 2022, 13, 1547 DOI: 10.1039/D1PY01616D

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