1472-09-9Relevant articles and documents
Cyclopropanation of Terminal Olefins Using Diazomethane/Palladium(II) Acetate
Suda, Minoru
, p. 714 (1981)
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Mechanism-based design and optimization of a catalytic electrophilic cyclopropanation without diazomethane
Tchawou, Augustin A. S. W.,Raducan, Mihai,Chen, Peter
supporting information, p. 180 - 191 (2017/11/27)
Iodomethylboron compounds, either the trifluoroborate or a boronic ester, cyclopropanate electron-rich olefins and unprotected allylic alcohols with Pd catalysts according to a novel, designed catalytic cycle. Proposed intermediates in a "diverted Heck" mechanism are observed by means of spectroscopic studies and by isolation and X-ray crystallographic characterization, which together with reaction kinetics point to a separation of rate-determining and product-determining steps, and a mechanism-based optimization of the yield, selectivity, and scope of the catalytic electrophilic cyclopropanation. The reaction with crystalline, air-stable, nonhygroscopic, and nontoxic reagents provides an alternative to Simmons-Smith-type reactions, as well as cyclopropanation procedures that require the use of diazomethane.
Breaking of the C-C bond of cyclobutanones by rhodium(I) and its extension to catalytic synthetic reactions
Murakami,Amii,Shigeto,Ito
, p. 8285 - 8290 (2007/10/03)
A study of rhodium(I)-catalyzed synthetic transformations involving selective breaking of the C-C bond α to the carbonyl group of cyclobutanones is described. Decarbonylation took place on treatment of a cyclobutanone with an equimolar amount of (Ph3