TY - JOUR
T1 - Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope
AU - Kozell, Vadym
AU - McLaughlin, Michael
AU - Strappaveccia, Giacomo
AU - Santoro, Stefano
AU - Bivona, Lucia Anna
AU - Aprile, Carmela
AU - Gruttadauria, Michelangelo
AU - Vaccaro, Luigi
PY - 2016/12/5
Y1 - 2016/12/5
N2 - In this contribution, we present a chemically efficient and sustainable protocol for the palladium-catalyzed copper-free Sonogashira cross-coupling reaction, based on the use of a heterogeneous catalytic system. This consists in the combination of a palladium catalyst on highly cross-linked thiazolidine network on silica and a polystyrene-supported base. The solid catalyst/base system acts as a palladium scavenger avoiding leaching of the metal and consequent product contamination. The reaction can be conducted in safe and easily recoverable acetonitrile/water azeotrope as reaction medium. This proved to be an efficient greener alternative to the classic toxic aprotic media commonly used in cross-coupling reaction, such as DMF and NMP. Acetonitrile/water azeotrope could be easily recovered and reused allowing the minimization of waste production. Our approach, based on the use of both a supported base and a supported catalyst, has proven to be efficient for the waste reduction, as proved by the low E-factor values achieved.
AB - In this contribution, we present a chemically efficient and sustainable protocol for the palladium-catalyzed copper-free Sonogashira cross-coupling reaction, based on the use of a heterogeneous catalytic system. This consists in the combination of a palladium catalyst on highly cross-linked thiazolidine network on silica and a polystyrene-supported base. The solid catalyst/base system acts as a palladium scavenger avoiding leaching of the metal and consequent product contamination. The reaction can be conducted in safe and easily recoverable acetonitrile/water azeotrope as reaction medium. This proved to be an efficient greener alternative to the classic toxic aprotic media commonly used in cross-coupling reaction, such as DMF and NMP. Acetonitrile/water azeotrope could be easily recovered and reused allowing the minimization of waste production. Our approach, based on the use of both a supported base and a supported catalyst, has proven to be efficient for the waste reduction, as proved by the low E-factor values achieved.
KW - Azeotrope media
KW - Green chemistry
KW - Heterogeneous catalysis
KW - Sonogashira reaction
KW - Waste minimization
UR - http://www.scopus.com/inward/record.url?scp=85002958302&partnerID=8YFLogxK
U2 - 10.1021/acssuschemeng.6b02170
DO - 10.1021/acssuschemeng.6b02170
M3 - Article
AN - SCOPUS:85002958302
SN - 2168-0485
VL - 4
SP - 7209
EP - 7216
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
IS - 12
ER -