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Activation of Carbon Dioxide by Silyl Triflate‐Based Frustrated Lewis Pairs
Author(s) -
Weicker Sarah A.,
Stephan Douglas W.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501904
Subject(s) - silylation , trifluoromethanesulfonate , chemistry , phosphine , alkyl , lewis acids and bases , medicinal chemistry , carbon dioxide , molecule , carbon fibers , frustrated lewis pair , organic chemistry , catalysis , materials science , composite number , composite material
Abstract Silyl triflates of the form R 4− n Si(OTf) n ( n =1, 2; OTf=OSO 3 CF 3 ) are shown to activate carbon dioxide when paired with bulky alkyl‐substituted Group 15 bases. Combinations of silyl triflates and 2,2,6,6‐tetramethylpiperidine react with CO 2 to afford silyl carbamates via a frustrated Lewis pair‐type mechanism. With trialkylphosphines, the silyl triflates R 3 Si(OTf) reversibly bind CO 2 affording [R′ 3 P(CO 2 )SiR 3 ][OTf] whereas when Ph 2 Si(OTf) 2 is used one or two molecules of CO 2 can be sequestered. The latter bis‐CO 2 product is favoured at low temperatures and by excess phosphine.