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Cooperative Catalysis of Cyclic Carbonate Ring Opening: Application Towards Non‐Isocyanate Polyurethane Materials
Author(s) -
Lombardo Vince M.,
Dhulst Elizabeth A.,
Leitsch Emily K.,
Wilmot Nathan,
Heath William H.,
Gies Anthony P.,
Miller Matthew D.,
Torkelson John M.,
Scheidt Karl A.
Publication year - 2015
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.201500313
Subject(s) - chemistry , isocyanate , trifluoromethanesulfonate , lewis acids and bases , catalysis , dimethyl carbonate , ring (chemistry) , polyurethane , polymer chemistry , carbonate , synergistic catalysis , diamine , lewis acid catalysis , organic chemistry , combinatorial chemistry
The reaction between cyclic carbonates and amines to produce hydroxyurethanes is an important alternative to current urethane chemistry. In order to address the issue of slow reaction rates, an efficient ring opening of cyclic carbonates with amines has been achieved utilizing cooperative catalysis. A new Lewis acid/Lewis base combination substantially decreases the reaction times for small molecule systems to reach complete conversion. Although triazabicyclodecene (TBD) has a substantial impact on the reaction rate, the addition of lithium triflate (LiOTf) as a co‐catalyst allows for the fastest ring opening reported in the current literature. Cooperative catalysis is also applied to the synthesis of polymers containing hydroxyurethane linkages and is able to achieve rapid conversion of the bis‐cyclic carbonate and diamine precursors when compared with the uncatalyzed reaction.