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Gold‐Catalyzed C−H Functionalization Polycondensation for the Synthesis of Aromatic Polymers
Author(s) -
King Eric R.,
Tropp Joshua,
Eedugurala Naresh,
Gonce Lauren E.,
Stanciu Sonia,
Azoulay Jason D.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011426
Subject(s) - reactivity (psychology) , chemistry , polymerization , catalysis , polymer chemistry , alkene , condensation polymer , monomer , alkyne , copolymer , polymer , nucleophile , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
Homogeneous gold (Au) complexes have demonstrated tremendous utility in modern organic chemistry; however, their application for the synthesis of polymers remains rare. Herein, we demonstrate the first catalytic application of Au complexes toward the polycondensation of alkyne‐containing comonomers and heteroarene nucleophiles. Polymerization occurs through successive intermolecular hydroarylation reactions to produce high molecular weight aromatic copolymers with 1,1‐disubstituted alkene backbone linkages. Clear correlations between the rate and degree of polymerization (DP) were established based on catalyst structure and counterion pairing, thus enabling polymerization reactions that proceeded with remarkable efficiency, high reactivity, and exceptional DPs. The reactivity is broad in scope, enabling the copolymerization of highly functionalized aromatic and aliphatic monomers. These results highlight the untapped utility of Au catalysis in providing access to new macromolecular constructs.