251635-75-3Relevant academic research and scientific papers
Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
supporting information, p. 5040 - 5045 (2019/07/03)
(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 7624 - 7629 (2019/10/02)
A highly reactive catalytic system for the carbonylative coupling of aryl iodides with alkenylaluminum reagents has been developed. Various β-substituted γ,δ-unsaturated ketones were produced under mild conditions in good to excellent yields even under ppm level of palladium catalyst. Notably, this also represents the first example on carbonylative transformation of alkenylaluminum compounds. Additionally, by the addition of zinc salt, the selectivity of the product can be modified.
Rhenium-catalyzed α-alkylation of enol acetates with alcohols or ethers
Umeda, Rui,Takahashi, Yuuki,Yamamoto, Takaaki,Iseki, Hideki,Osaka, Issey,Nishiyama, Yutaka
supporting information, p. 92 - 101 (2018/11/01)
When benzylic and allylic alcohols were treated with enol acetate in the presence of a catalytic amount of a rhenium complex, ReBr(CO)5, the carbon-carbon bond formation of the alcohols and enol acetate smoothly proceeded to give the corresponding ketones and aldehyde in moderate to good yields. For the reaction of allylic alcohols, γ,δ-unsaturated carbonyl compounds were obtained in good yields. When ethers were used instead of alcohols as the alkylated agent, two alkyl moieties on the ethers were utilized on the reaction.
Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts
Wu, Chunlin,Yue, Guizhou,Nielsen, Christian Duc-Trieu,Xu, Kai,Hirao, Hajime,Zhou, Jianrong
supporting information, p. 742 - 745 (2016/02/05)
Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.
Triflic acid promoted direct α-alkylation of unactivated ketones using benzylic alcohols via in situ formed acetals
Koppolu, Srinivasa Rao,Naveen, Naganaboina,Balamurugan, Rengarajan
supporting information, p. 6069 - 6078 (2014/07/21)
Direct α-alkylation of unactivated ketones using benzylic alcohols as electrophiles has been achieved at room temperature. This reaction takes place via in situ formed acetal using triflic acid and trimethyl orthoformate. It is believed that methyl vinyl
Enone-alkyne reductive coupling: A versatile entry to substituted pyrroles
Thompson, Benjamin B.,Montgomery, John
supporting information; experimental part, p. 3289 - 3291 (2011/09/13)
The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dica
Copper(I) iodide dimethyl sulfide catalyzed 1,4-addition of alkenyl groups from alkenyl-alkylzincate reagents
El-Batta, Amer,Bergdahl, Mikael
, p. 1761 - 1765 (2008/02/05)
The presence of catalytic quantities of the copper(I) iodide dimethyl sulfide complex {(CuI)4(SMe2)3} with alkenyl-alkylzincate reagents allows for the complete chemoselective 1,4-addition of various alkenyl groups to a nu
A new reaction of the phenylhydrazones of 1,5-diketones. Synthesis of dihydropyran derivatives
Moskovkina
, p. 22 - 27 (2007/10/03)
It was shown that the monophenylhydrazones of 1,5-diketones are converted by reduction with borohydride followed by treatment of the obtained hydrazino alcohols with acidic agents into derivatives of dihydropyran with the elimination of phenylhydrazine as
Conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds catalyzed by a cationic rhodium complex
Oi, Shuichi,Honma, Yoshio,Inoue, Yoshio
, p. 667 - 669 (2007/10/03)
A novel, additive-free, and clean conjugate addition reaction of organosiloxanes to α,β-unsaturated carbonyl compounds catalyzed by a cationic rhodium complex in water-containing solvent has been developed. A plausible reaction mechanism involving the add
Carbon-carbon bond formation by reactions of allylic alcohol with enoxysilane in the presence of Ir-complex
Matsuda, Isamu,Wakamatsu, Shogo,Komori, Ken-Ichi,Makino, Tatsuya,Itoh, Kenji
, p. 1043 - 1046 (2007/10/03)
Substitution of allylic alcohols to form a carbon-carbon bond is accomplished by a simple reaction of the allylic alcohol itself with an enoxysilane, catalyzed by [Ir(cod)(PPh3)2]X which is activated by H2 molecule. The anion part X of the complexes plays an important role to enhance the rate and product yields of the reactions. The efficacy of the catalyst increases with switching X in the order of PF6-4--.
