24892-77-1Relevant articles and documents
Base-promoted [1,4]-Wittig rearrangement of chalcone-derived allylic ethers leading to aromatic β-benzyl ketones
Gao, Pei-Sen,Ye, Fei,Dong, Xiao-Yun,Chen, Yun,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
, p. 33818 - 33822 (2015)
n-BuLi-promoted [1,4]-Wittig rearrangement of allylic ethers was developed successfully in this work, in which the Wittig rearrangement reaction provided a facile approach to the synthesis of aromatic β-benzyl ketones under mild reaction conditions.
Addition reactions of organic carbanion equivalents via hydrazones in water
Wang, Yi-Zhan,Liu, Qi,Cheng, Liang,Yu, Song-Chen,Liu, Li,Li, Chao-Jun
supporting information, (2021/01/11)
The addition of organometallic reagents to unsaturated bonds is one of the most powerful tools for carbon–carbon bond formations. Alkylation through organometallic reagents requires stoichiometric quantity of metal and tedious anhydrous operation in most cases. Here, we report “umpolung” nucleophilic additions of hydrazones to Michael acceptors, carbonyls and imines in water. Under the catalysis of ruthenium(II), the addition reactions could be carried out in pure water to provide various alkylation products in moderate to good yields.
Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C-C σ-Bonds in Cyclopropanes with iPrOH
Chen, Chen,Feng, Shiyu,Chan, Kin Shing
, p. 2582 - 2589 (2019/07/02)
A new rhodium porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C-C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give the corresponding acyclic alkanes and regenerate rhodium(II) metalloporphyrin radical.
One-Pot Photomediated Giese Reaction/Friedel-Crafts Hydroxyalkylation/Oxidative Aromatization to Access Naphthalene Derivatives from Toluenes and Enones
Liu, Haiwang,Ma, Lishuang,Zhou, Rong,Chen, Xuebo,Fang, Weihai,Wu, Jie
, p. 6224 - 6229 (2018/06/11)
Value-added chemicals, γ-aryl ketones and naphthalenes, were conveniently synthesized from readily available toluenes and enones through the synergistic combination of photoredox and Lewis acid catalysis. The direct synthesis of γ-aryl ketones represents a rare example of Giese reactions between benzylic C(sp3)-H and enones that avoids the use of prefunctionalized metallic nucleophiles. Naphthalene derivatives were accessed through a one-pot Giese reaction/Friedel-Crafts hydroxyalkylation/oxidative aromatization sequential transformation.
Ligand-accelerated Pd-catalyzed ketone γ-arylation via C-C cleavage with aryl chlorides
Ziadi, Asraa,Martin, Ruben
supporting information; experimental part, p. 1266 - 1269 (2012/04/23)
A highly efficient Pd-catalyzed arylative ring expansion of cyclobutanols via C-C bond cleavage is presented. The method allows the coupling of aryl chlorides at low catalyst loadings with a wide range of functional groups and substitution patterns, thus constituting a straightforward alternative for preparing rather elusive γ-arylated ketones.
Free radical-promoted conjugate addition of activated bromo compounds using titanocene(III) chloride as the radical initiator
Mandal, Samir Kumar,Jana, Samaraesh,Roy, Subhas Chandra
, p. 6115 - 6117 (2007/10/03)
Free radical-promoted conjugate addition of activated bromo compounds to α,β-unsaturated ketones and reactive α,β-unsaturated esters has been described using titanocene(III) chloride (Cp2TiCl) as the radical initiator. Cp2TiCl was prepared in situ from commercially available Cp2TiCl2 and activated zinc dust in THF.
Generation of organotantalum reagents and conjugate addition to enones
Shibata, Ikuya,Kano, Takeyoshi,Kanazawa, Nobuaki,Fukuoka, Shoji,Baba, Akio
, p. 1389 - 1392 (2007/10/03)
A superior method of conjugate allylation: The transmetalation of allyltin compounds with TaCl5 yielded active tantalum reagents for conjugate addition to enones. Even bulky allyl moieties could be introduced to enones in this manner (see scheme). Both cyclic and acyclic enones reacted facilely under extremely mild conditions.
Palladium-catalysed asymmetric arylation of tert-cyclobutanols via enantioselective C-C bond cleavage
Nishimura, Takahiro,Matsumura, Satoshi,Maeda, Yasunari,Uemura, Sakae
, p. 50 - 51 (2007/10/03)
Palladium-catalysed arylation of tert-cyclobutanols with aryl bromide involving enantioselective C-C bond cleavage affords chiral ketones with moderate to good enantiose-lectivity.
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.
