81707-26-8Relevant articles and documents
Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: Co-catalysis controls regioselectivity
Zhao, Yang,Weix, Daniel J.
supporting information, p. 48 - 51 (2014/01/23)
Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via TiIII-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
Reaction of 1-Substituted Indenes with Diborane or N-Bromoacetamide in Protic Solvents. The Effect of the Substituent on the Stereochemistry of Addition
Miura, Masahiro,Yoshida, Masaya,Nojima, Masatomo,Kusabayashi, Shigekazu
, p. 79 - 84 (2007/10/02)
The reaction of 1-substituted indenes with diborane or N-bromoacetamide (NBA) in protic solvents has been investigated to determine the effect of an increase of steric bulk of the substituent on the stereochemical course of addition.In the hydroboration reaction the proportion of the products via attack by diborane from the less hindered side increases, as the steric bulk of the substituent at C-1 increases.The reaction with NBA in aqueous dioxan, followed by acetylation, gave a mixture of 3-substituted-1-acetoxy-2-bromoindans with trans, trans and trans,cis-configuration: 1-phenylindene gave mainly trans, trans-1-acetoxy-2-bromo-3-phenylindan, while trans,cis-1-acetoxy-2-bromo-3-methylindan was the maior product in the case of 1-methylindene.
