123200-56-6Relevant academic research and scientific papers
Copper-catalyzed conjugate addition of in situ formed alkyl boranes to α,β-unsaturated ketones
Mravec, Bernard,Plevová, Kristína,?ebesta, Radovan
, p. 295 - 302 (2019)
Abstract: Conjugate addition of in situ formed organometallic reagents to α,β-unsaturated carbonyl compounds provides an efficient way to generate new C–C bonds. We show optimization of the copper-catalyzed conjugate addition of alkylboranes, which were formed directly in the reaction mixture by hydroboration of alkenes. We have improved the reaction conditions by employing “greener”, less hygroscopic, and higher boiling solvent, 2-methyltetrahydrofuran. We have also broadened the scope of the reaction. Furthermore, chiral ferrocenyl carbene ligands were assessed in the enantioselective version of the transformation with medium enantioselectivity 67:33 e.r.
Neutral-eosin Y-catalyzed regioselective hydroacylation of aryl alkenes under visible-light irradiation
Liu, Haiwang,Xue, Fei,Wang, Mu,Tang, Xinxin,Wu, Jie
supporting information, p. 406 - 410 (2020/12/30)
Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.
Copper-catalyzed conjugate additions of alkylboranes to aryl α,β-Unsaturated Ketones
Ohmiya, Hirohisa,Shido, Yoshinori,Yoshida, Mika,Sawamura, Masaya
experimental part, p. 928 - 930 (2011/12/05)
Conjugate addition of alkylboron compounds (alkyl-9-BBN) to aryl α,β-unsaturated ketones proceeded in the presence of a catalytic amount (10 mol%) of [(IPr)CuCl] and t-BuOK. The alkylboranes are available through alkene hydroboration, and thus the overall process represents a reductive conjugate addition of alkenes to enone derivatives. A variety of functional groups are tolerated in both the alkenes and the α,β- unsaturated ketones.
Synthetically useful desulfurisation reactions of heteroaryl sulfoxide conjugate adducts
Casey,Gairns,Walker
, p. 1725 - 1728 (2007/10/03)
Efficient desulfurisation reactions of the conjugate addition products derived from 1-methyl-2-imidazolyl and 2-pyridyl sulfoxides have been achieved. Hydrodesulfurisation was effected either by reduction of the sulfoxides to sulfides, followed by treatment with Raney nickel, or more reliably by reaction of either the sulfides or the sulfoxides with nickel boride. Pyrolytic elimination furnished alkenes stereoselectively on heating the sulfoxides to reflux in toluene or chloroform.
Isolation and characterisation of aromatic substituted olefinic compounds from the starfish Pteraster militaris
Yayli, Nurettin
, p. 556 - 561 (2007/10/03)
Two series of the polyaromatic coumpound (1-6 and 7-14) have been isolated from the starfish Pteraster militaris after column chromatography over Amberlite XAD-2 resin.Their structures have been established by spectroscopic means and confirmed as 2,4-diph
Conjugate Addition Reactions of Organosamarium Species via in Situ Transmetalation to Cu(I) Salts
Totleben, Michael J.,Curran, Dennis P.,Wipf, Peter
, p. 1740 - 1744 (2007/10/02)
Preformed organosamarium species, available by reduction of aryl or alkyl halides with SmI2, were treated with copper(I) salts to effect in situ transmetalation and conjugate addition to enones.In a series of copper(I) salts, CuI*P(OEt)3 gave best results in combination with 2 equiv of organosamarium reagent.This new method allows the multiple formation of carbon-carbon bonds through a combination of radical and cuprate chemistry.
