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A Resin‐Bound Peptoid as a Recyclable Heterogeneous Catalyst for Oxidation Reactions
Author(s) -
Stamatin Yekaterina,
Maayan Galia
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901739
Subject(s) - peptoid , chemistry , catalysis , cooperativity , intramolecular force , combinatorial chemistry , dimer , trimer , polymer chemistry , organic chemistry , peptide , biochemistry
Reusable solid‐grafted catalysts have environmental and economical advantages over soluble catalysts. Numerous catalysts, including peptides, were immobilized on solid supports to enable their recyclability. Nevertheless, the few catalytic peptoids – N‐substituted glycine oligomers – reported to date were only used off‐resin. The soluble peptoids BT and DI , a trimer and dimer having two catalytic side‐chains, were developed as bio‐inspired oxidation catalysts. BT has an additional structure‐directing group, which enables intramolecular cooperativity between the two catalytic groups (“intra‐peptoid” mode). Thus, it catalyzes the oxidation of primary alcohols with much higher efficiency than DI . Herein, we present resin‐bound BT and DI ( TG‐BT and TG‐DI ) as the first insoluble and recyclable catalytic peptoids. We discovered that though TG‐BT also operates through the intra‐peptoid cooperativity mode, it is less efficient than BT , even after several cycles. On the other hand, TG‐DI is far more active than DI and can be recycled several times to enable a much higher turn‐over‐number. Our studies revealed that TG‐DI operates through an intra‐resin cooperativity mode, and this enables its high activity compared with DI , BT and TG‐BT .