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Synthesis of carbamates from carbon dioxide promoted by organostannanes and alkoxysilanes
Author(s) -
Germain Nicolas,
Hermsen Marko,
Schaub Thomas,
Trapp Oliver
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3733
Subject(s) - chemistry , orthosilicate , carbon dioxide , alkyl , alkylation , yield (engineering) , catalysis , organic chemistry , aryl , reaction mechanism , tetraethyl orthosilicate , thermodynamics , physics
A cooperative methoxy transfer between orthosilicate esters and organotin oxides was developed for the synthesis of various N ‐alkyl and N ‐aryl carbamates from carbon dioxide in up to 97% isolated yield. The reaction is highly selective and N ‐alkylated amines are not observed. Density functional theory calculations of the reaction were performed and, together with NMR observations, a plausible mechanism featuring the catalytic regeneration of dialkyltin dialkoxide is proposed.