scholarly journals Deep Eutectic Solvent as a Sustainable Medium for C–C Bond Formation Via Multicomponent Radical Conjugate Additions

2021 ◽  
Author(s):  
Beatriz Saavedra ◽  
Diego J. Ramón
Keyword(s):  
Bond Formation ◽  
Deep Eutectic Solvent ◽  
Conjugate Additions

Carbon–carbon bond formation in acid deep eutectic solvent: chalcones synthesis via Claisen–Schmidt reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (49) ◽  
pp. 43740-43747 ◽  
Author(s):  
Matteo Tiecco ◽  
Raimondo Germani ◽  
Fabio Cardellini
Keyword(s):  
Bond Formation ◽  
Deep Eutectic Solvent ◽  
Basic Catalyst ◽  
Schmidt Reaction ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Claisen–Schmidt reaction in acid deep eutectic solvent without the use of acid or basic catalyst.

scholarly journals Asymmetric Remote C–H Functionalization: Use of Internal Olefins in Tandem Hydrometallation–Isomerization–Asymmetric Conjugate Addition Sequences

2015 ◽  
Vol 68 (3) ◽  
pp. 401 ◽  
Author(s):  
Laura Mola ◽  
Mireia Sidera ◽  
Stephen P. Fletcher
Keyword(s):  
Bond Formation ◽  
Conjugate Addition ◽  
Conjugate Additions ◽  
Schwartz Reagent ◽  
Isomerization Mechanism ◽  
Catalytic Asymmetric ◽  
A Chain ◽  
Chain Walking

We describe catalytic asymmetric C–C formation using terminal alkyl-metal nucleophiles generated from internal olefins through a ‘chain-walking’ isomerization mechanism. Hydrometallation of internal olefins with the Schwartz reagent gives the least hindered alkyl-zirconocene after thermal (60°C in THF) isomerization. After switching the solvent from THF to dichloromethane, the alkyl-zirconocenes can be used in copper-catalyzed asymmetric conjugate additions. Addition to a variety of cyclic α,β-unsaturated species were achieved in modest (22–50 %) yield with high (84–92 % ee) enantioselectivity. This work demonstrates that remote C–H functionalization coupled with asymmetric C–C bond formation is possible, but the present procedures are limited in terms of yield and olefin scope.

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