89914-05-6Relevant articles and documents
Regioselective Simmons-Smith-type cyclopropanations of polyalkenes enabled by transition metal catalysis
Werth, Jacob,Uyeda, Christopher
, p. 1604 - 1609 (2018/02/14)
A [i-PrPDI]CoBr2 complex (PDI = pyridine-diimine) catalyzes Simmons-Smith-type reductive cyclopropanation reactions using CH2Br2 in combination with Zn. In contrast to its non-catalytic variant, the cobalt-catalyzed cyclopropanation is capable of discriminating between alkenes of similar electronic properties based on their substitution patterns: monosubstituted > 1,1-disubstituted > (Z)-1,2-disubstituted > (E)-1,2-disubstituted > trisubstituted. This property enables synthetically useful yields to be achieved for the monocyclopropanation of polyalkene substrates, including terpene derivatives and conjugated 1,3-dienes. Mechanistic studies implicate a carbenoid species containing both Co and Zn as the catalytically relevant methylene transfer agent.
REACTION OF DIAZOALKANES WITH UNSATURATED COMPOUNDS COMMUNICATION 1. CYCLOPROPANATION OF OLEFINS WITH DIAZOMETHANE IN THE PRESENCE OF COPPER COMPOUDS
Nefodov, O. M.,Dolgii, I. E.,Tomilov, Yu. V.,Bordakov, V. G.
, p. 103 - 108 (2007/10/02)
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