An inexpensive and recyclable silver-foil catalyst for the cyclopropanation of alkenes with diazoacetates under mechanochemical conditions.
The diastereoselective cyclopropanation of various alkenes with diazoacetate derivatives can be achieved under mechanochemical conditions using metallic silver foil and a stainless-steel vial and ball system. This solvent-free method displays analogous reactivity and selectivity to solution-phase reactions without the need for slow diazoacetate addition or an inert atmosphere. The heterogeneous silver-foil catalyst system is easily recyclable without any appreciable loss of activity or selectivity being observed. The cyclopropanation products were obtained with excellent diastereoselectivities (up to 98:2 d.r.) and in high yields (up to 96 %).
Department of Chemistry, University of Cincinnati, Cincinnati, OH 45220 (USA).
Longrui
L
Chen
Department of Chemistry, University of Cincinnati, Cincinnati, OH 45220 (USA).
Mark O
MO
Bovee
Department of Chemistry, Rochester Institute of Technology, Rochester, NY 14623 (USA).
Betsegaw E
BE
Lemma
Department of Chemistry, Rochester Institute of Technology, Rochester, NY 14623 (USA).
Kimberlee S M
KS
Keithley
Department of Chemistry, Rochester Institute of Technology, Rochester, NY 14623 (USA).
Sara L
SL
Pilson
Department of Chemistry, Rochester Institute of Technology, Rochester, NY 14623 (USA). mgcsch@rit.edu.
Michael G
MG
Coleman
Department of Chemistry, University of Cincinnati, Cincinnati, OH 45220 (USA). james.mack@uc.edu.
James
J
Mack
cycloaddition; green chemistry; heterogeneous catalysis; solid-phase synthesis; sustainable chemistry