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Polymer‐ and Silica‐Supported Iron BPMEN‐Inspired Catalysts for CH Bond Functionalization Reactions
Author(s) -
Feng Yan,
Moschetta Eric G.,
Jones Christopher W.
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402461
Subject(s) - catalysis , surface modification , cyclohexane , chemistry , ligand (biochemistry) , cyclooctane , organic chemistry , polymer chemistry , biochemistry , receptor
Abstract Direct catalytic CH bond functionalization is a key challenge in synthetic chemistry, with many popular CH activation methodologies involving precious‐metal catalysts. In recent years, iron catalysts have emerged as a possible alternative to the more common precious‐metal catalysts, owing to its high abundance, low cost, and low toxicity. However, iron catalysts are plagued by two key factors: the ligand cost and the low turnover numbers (TONs) typically achieved. In this work, two approaches are presented to functionalize the popular N 1 , N 2 ‐dimethyl‐ N 1 , N 2 ‐bis(pyridin‐2‐ylmethyl)ethane‐1,2‐diamine (BPMEN) ligand, so that it can be supported on porous silica or polymer resin supports. Four new catalysts are prepared and evaluated in an array of catalytic CH functionalization reactions by using cyclohexane, cyclohexene, cyclooctane, adamantane, benzyl alcohol, and cumene with aqueous hydrogen peroxide. Catalyst recovery and recycling is demonstrated by using supported catalysts, which allows for a modest increase in the TON achieved with these catalysts.