90499-97-1Relevant academic research and scientific papers
Friedel–Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers
Jirgensons, Aigars,Lielpetere, Anna
, (2020/07/27)
The electrochemical activation of stannylmethyl ethers was exploited for Friedel–Crafts alkylation of arenes at near-neutral conditions. Single cell anodic oxidation of stannylmethyl ethers leads to oxonium ions which fragment to carbenium ions in the pre
Dearomative [4+2] Cycloaddition of Oxindole-Embedded ortho-Quinone Methides with 2,5-Dialkylfurans
Shen, Yao-Bin,Li, Shuai-Shuai,Liu, Xicheng,Yu, Liping,Liu, Qing,Xiao, Jian
supporting information, (2019/02/19)
2,5-Dialkylfurans were facilely converted to pharmaceutically significant spiro[chroman-4,3′-oxindole] scaffolds via an organocatalytic dearomative [4+2] cycloaddition with oxindole-embedded ortho-quinone methides. This method featured mild reaction conditions, simple operation, good yields, and excellent diastereoselectivities.
Silylated cyclopentadienes as competent silicon Lewis acid catalysts
Radtke, M. Alex,Lambert, Tristan H.
, p. 6406 - 6410 (2018/08/12)
The synthesis and characterization of silicon Lewis acid complexes that incorporate highly electron-deficient cyclopentadienes is reported. Several pentacarboxycyclopentadienyl and monocarboxytetracyanocyclopentadienyl complexes were prepared. A comparison of their reactivities for catalysis of the allylation of an electron-deficient benzaldehyde was established. The use of a monocarboxytetracyano silylium donor was shown to be effective for the allylation or arylation of a variety of electrophiles via an anion abstraction pathway.
CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step
Makarov, Anton S.,Kekhvaeva, Anna E.,Hall, Christopher J.J.,Price, Daniel R.,Trushkov, Igor V.,Uchuskin, Maxim G.
, p. 7042 - 7053 (2017/11/13)
A CuBr2-catalyzed alkylation of furans with a broad scope of benzyl alcohols and benzaldehydes is reported. Reaction proceeds efficiently under mild reaction conditions requiring no inert atmosphere or other precautions. Moreover, it is shown that CuBr2 catalyzes domino reactions of furans with benzyl alcohols or benzaldehydes bearing a nucleophilic moiety in the ortho-position. These protocols offer a practical approach to densely substituted heterocyclic motifs from easily available furans.
Simple Method for sp2-sp3 and sp3-sp3 Carbon-Carbon Bond Activation in 2-Substituted 1,3-Diketones
Aoyama, Tadashi,Hayakawa, Mamiko,Kubota, Sho,Ogawa, Sumire,Nakajima, Erika,Mitsuyama, Emi,Iwabuchi, Taku,Kaneko, Haruki,Obara, Rina,Takido, Toshio,Kodomari, Mitsuo,Ouchi, Akihiko
supporting information, p. 2945 - 2956 (2015/09/28)
Simple and efficient methods were developed for sp2-sp3 and sp3-sp3 C-C bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Bronsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp3-sp3 C-C bond of the dione alkylated the aromatic compound.
Organocatalytic friedel-crafts benzylation of heteroaromatic and aromatic compounds via an SN1 pathway
Watanabe, Naruhisa,Matsugi, Aoi,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
supporting information, p. 438 - 442 (2014/03/21)
The Friedel-Crafts-type benzylation of various π-excessive heteroaromatic and aromatic compounds with trityl or benzhydryl halides was efficiently promoted by a thiourea catalyst. This is a novel example of thiourea catalysis of aromatic alkylation by way
Commercially available simple ionic liquids-promoted dehydrative carbon-carbon bond-forming reaction of diarylmethanols and triarylmethanols with pyrroles, thiophene, furan and indoles
Funabiki, Kazumasa,Komeda, Takuya,Nishikawa, Kouhei,Yamada, Kentaro,Kubota, Yasuhiro,Matsui, Masaki
, p. 9245 - 9252 (2015/02/19)
Two commercially available simple ionic liquids, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate and 1-ethyl-2,3-dimethylimidazolium trifluoromethansulfonate, effectively promote the solvent-free dehydrative carbon-carbon (C-C) bond-forming reaction
First example of a heterobimetallic 'Pd-Sn' catalyst for direct activation of alcohol: Efficient allylation, benzylation and propargylation of arenes, heteroarenes, active methylenes and allyl-Si nucleophiles
Das, Debjit,Pratihar, Sanjay,Roy, Ujjal Kanti,Mal, Dipakranjan,Roy, Sujit
experimental part, p. 4537 - 4542 (2012/07/17)
Arenes, heteroarenes, 1,3-dicarbonyls and organosilicon nucleophiles undergo highly efficient alkylation with allylic, propargylic and benzylic alcohols in the presence of a new 'Pd-Sn' bimetallic catalyst in nitromethane; water being the sole byproduct.
Direct alkylation of aromatics using alcohols in the presence of NaHSO 4/SiO2
Sato, Yuta,Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
supporting information; experimental part, p. 7077 - 7081 (2012/08/28)
Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss.
An efficient and general iron-catalyzed C-C bond activation with 1,3-dicarbonyl units as a leaving groups
Li, Huanrong,Li, Wenjuan,Liu, Weiping,He, Zhiheng,Li, Zhiping
supporting information; experimental part, p. 2975 - 2978 (2011/05/05)
(Chemical Equation Presented) With our compliments: The 1,3-dicarbonyl unit has been shown to be a new and useful leaving group for iron-catalyzed bond cleavage (see scheme). This new strategy can complement the traditional Friedel-Crafts reaction and was applied in the synthesis of indene derivatives.
