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N‐Heterocyclic Olefins as Robust Organocatalyst for the Chemical Conversion of Carbon Dioxide to Value‐Added Chemicals
Author(s) -
Saptal Vitthal B.,
Bhanage Bhalchandra M.
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600467
Subject(s) - chemistry , formylation , nucleophile , carboxylation , organic chemistry , organocatalysis , adduct , carbon dioxide , catalysis , enantioselective synthesis
In this report, the activity of N‐heterocyclic olefins (NHOs) as a newly emerging class of organocatalyst is investigated for the chemical fixation of carbon dioxide through reactions with aziridines to form oxazolidinones and the N ‐formylation of amines with polymethylhydrosiloxane (PMHS) or 9‐borabicyclo[3.3.1]nonane (9‐BBN) as the reducing agent under mild conditions. The exocyclic carbon atoms of NHOs are highly nucleophilic owing to the electron‐donating ability of the two nitrogen atoms. This high nucleophilicity of the NHOs activates CO 2 molecules to form zwitterionic NHO–carboxylate (NHO–CO 2 ) adducts, which are active in formylation reactions as well as the carboxylation of aziridines to oxazolidinones.