Premium
A Pd(II)‐Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β‐Disubstituted Enones
Author(s) -
Heintz Patrick M.,
Schumacher Brian P.,
Chen Minda,
Huang Wenyu,
Stanley Levi M.
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900894
Subject(s) - catalysis , chemistry , conjugate , covalent bond , nucleophile , palladium , diamine , covalent organic framework , yield (engineering) , organic chemistry , bipyridine , linker , aldol reaction , combinatorial chemistry , polymer chemistry , materials science , mathematical analysis , mathematics , computer science , crystal structure , metallurgy , operating system
A palladium(II)‐functionalized covalent organic framework (Pd@TpBpy COF) constructed from 1,3,5‐triformylphloroglucinol (Tp) and [2,2′‐bipyridine]‐5,5′‐diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions of an array of stereoelectronically diverse arylboronic acid nucleophiles to β,β‐disubstituted enones form a variety of ketones containing benzylic all‐carbon quaternary centers in up to 92 % isolated yield. Studies on the recyclability of Pd@TpBpy COF show this catalyst remains active through at least 7 cycles and shows superior stability to related MOF catalysts with bipyridine linker units.