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Sequential ATRA/Reductive Cyclopropanation Reactions with a Ruthenium Catalyst in the Presence of Manganese
Author(s) -
FernándezZúmel Mariano A.,
Buron Charlotte,
Severin Kay
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100175
Subject(s) - cyclopropanation , chemistry , catalysis , ruthenium , manganese , turnover number , substrate (aquarium) , medicinal chemistry , ethyl diazoacetate , organic chemistry , combinatorial chemistry , oceanography , geology
Atom‐transfer radical addition (ATRA) reactions of ethyl trichloroacetate, dichloromalononitrile, or diethyl 2,2‐dichloromalonate with olefins followed by dechlorination have provided functionalized cyclopropanes in one step. The Ru III complex [Cp*RuCl 2 (PPh 3 )] was used as a catalyst precursor and commercial Mn powder as reducing agent. Reactions with the less activated substrate ethyl dichloroacetate gave ATRA products with high turnover numbers but cyclopropanation was not observed.