Download PDF
Synfacts 2018; 14(10): 1097
DOI: 10.1055/s-0037-1610983
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Formylation of Amines with CO2 Using a Polymeric Frustrated Lewis Pair

Contributor(s):
Yasuhiro Uozumi
,
Go Hamasaka
Chen L, Liu R, Yan Q. * Fudan University, Shanghai, P. R. of China
Polymer Meets Frustrated Lewis Pair: Second-Generation CO2-Responsive Nanosystem for Sustainable CO2 Conversion.

Angew. Chem. Int. Ed. 2018;
57: 9336-9340
CrossrefPubMedGoogle Scholar
Further Information

Publication History

Publication Date:
17 September 2018 (online)

 
 PDF Download Permissions and Reprints

Key words

frustrated Lewis pair - boranes - phosphines - formylation - amines - carbon dioxide

Significance

A polymeric carbon dioxide bridged frustrated Lewis pair (A) was prepared by treatment of an electron-deficient triarylborane immobilized on polystyrene with a sterically demanding triarylphosphine immobilized on polystyrene in the presence of CO2 (eq. 1). The polymeric frustrated Lewis pair A catalyzed the formylation of amines with carbon dioxide in the presence of phenylsilane at room temperature to give the corresponding formamides in up to 99% yield (eq. 2). The turnover number for the formylation reached as high as 14800.


#

Comment

The polymeric frustrated Lewis pair A was characterized by 11B, 19F, and 31P NMR, DLS, TEM, FT-IR, UV-Vis, and conductivity measurements. In the formylation of diethylamine, morpholine, aniline, benzophenone imine, or imidazole, the catalyst was reused seven times with slight loss of the catalytic activity.


#
#


   Permissions and Reprints