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NHC‐Ag/Pd‐Catalyzed Reductive Carboxylation of Terminal Alkynes with CO 2 and H 2 : A Combined Experimental and Computational Study for Fine‐Tuned Selectivity
Author(s) -
Yu Dingyi,
Zhou Feng,
Lim Diane S. W.,
Su Haibin,
Zhang Yugen
Publication year - 2017
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.201601785
Subject(s) - catalysis , selectivity , carboxylation , terminal (telecommunication) , chemistry , palladium , combinatorial chemistry , organic chemistry , computer science , telecommunications
Reductive carboxylation of terminal alkynes utilizing CO 2 and H 2 as reactants is an interesting and challenging transformation. Theoretical calculations indicated it would be kinetically possible to obtain cinnamic acid, the reductive carboxylation product, from phenylacetylene in a CO 2 /H 2 system with an N‐heterocyclic carbene (NHC)‐supported Ag/Pd bimetallic catalysts through competitive carboxylation/hydrogenation cascade reactions in one step. These calculations were verified experimentally with a poly‐NHC‐supported Ag/Pd catalyst. By tuning the catalyst composition and reaction temperature, phenylacetylene was selectively converted to cinnamic acid, hydrocinnamic acid, or phenylpropiolic acid in excellent yields.