55075-31-5Relevant academic research and scientific papers
Chlorotrimethylsilane - A novel catalyst in friedel-crafts reaction
Srivastava, Neeta,Kumar, Atul,Dwivedy, Indra,Ray, Suprabhat
, p. 2877 - 2883 (1997)
In the Friedel-Crafts condensation of diaryl carbinol with substituted phenols, the use of chlorotrimethylsilane (CTMS) as catalyst, leads to the formation of triarylmethanes under mild conditions. 6-Methoxy- 1,2,3,4- tetrahydronaphthalen- 1-ol under similar condition, on condensation with o- cresol, gives 1-(4-hydroxy-3-methyl phenyl)-6-methoxy-1,2,3,4- tetrahydronaphthalene.
Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides
Cao, Weidi,Feng, Xiaoming,Jiang, Mingyi,Li, Xiangqiang,Zhan, Tangyu
supporting information, (2020/06/17)
A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.
[4 + 2]-Cycloaddition and 1,4-Addition of ortho-Quinone Methides by a Chiral Crotyl Silane
Wong, Christopher R.,Hummel, Gerald,Cai, Yongqi,Schaus, Scott E.,Panek, James S.
supporting information, p. 32 - 35 (2019/01/04)
Anhydrous FeCl3 in the presence of 2,6-lutidine promotes the substrate-controlled enantioselective [4 + 2]-cycloaddition and crotylation reaction between an enantioenriched (S,E)-crotyl silane and in situ generated ortho-quinone methides (oQMs)
A base-promoted cascade reaction of α,β-unsaturated: N -tosylhydrazones with o -hydroxybenzyl alcohols: Highly regioselective synthesis of N-sec -alkylpyrazoles
Chen, Lian-Mei,Zhao, Juan,Xia, An-Jie,Guo, Xiao-Qiang,Gan, Ya,Zhou, Chuang,Yang, Zai-Jun,Yang, Jun,Kang, Tai-Ran
supporting information, p. 8561 - 8570 (2019/10/02)
An efficient method for the synthesis of N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcohols has been developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20:1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcohols, α,β-unsaturated N-tosylhydrazones and saturated N-tosylhydrazones also took place to afford pyrazoles in good yields. This reaction offers a new route to triarylmethanes with a simple operation and is applicable for large-scale synthesis.
A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans
Abaev, Vladimir T.,Chalikidi, Petrakis N.,Kekhvaeva, Anna E.,Makarov, Anton S.,Trushkov, Igor V.,Uchuskin, Maxim G.
, p. 3747 - 3757 (2019/09/30)
The Br?nsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans
Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols
Gharui, Chandan,Behera, Debasmita,Pan, Subhas Chandra
supporting information, p. 4502 - 4508 (2018/11/10)
An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).
Multicomponent Condensation Reactions via ortho-Quinone Methides
Allen, Emily E.,Zhu, Calvin,Panek, James S.,Schaus, Scott E.
, p. 1878 - 1881 (2017/04/11)
Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels - Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels - Alder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.
A simple synthesis of benzofurans by acid-catalyzed domino reaction of salicyl alcohols with N-tosylfurfurylamine
Merkushev, Anton A.,Strel'nikov, Vladimir N.,Uchuskin, Maxim G.,Trushkov, Igor V.
, p. 6523 - 6529 (2017/10/17)
A simple route to polysubstituted benzofurans based on the domino reaction of commercial or easily available salicyl alcohols with N-protected furfurylamine has been designed and developed. The reaction was found to proceed with reasonable yields under heating of substrates in acetic acid in the presence of catalytic amount of conc. HCl when tosyl was used as protecting group.
Bifunctional Amine-Squaramide Catalyzed Friedel–Crafts Alkylation Based on ortho-Quinone Methides in Oil-Water Phases: Enantioselective Synthesis of Triarylmethanes
Wang, Yifeng,Zhang, Cheng,Wang, Haojiang,Jiang, Yidong,Du, Xiaohua,Xu, Danqian
supporting information, p. 791 - 797 (2017/03/11)
An efficient enantioselective Friedel–Crafts alkylation reaction of electron-rich β-naphthol with in situ generated ortho-quinone methides catalyzed by chiral bifunctional amine-squaramide catalysts has been developed. The chiral triarylmethane derivative
Organocatalytic Phosphonylation of in Situ Formed o-Quinone Methides
Huang, Hai,Kang, Jun Yong
supporting information, p. 5988 - 5991 (2017/11/10)
A new class of Br?nsted acid catalysts based on N-heterocyclic phosphorodiamidic acids (NHPAs) has been developed. The NHPA catalyst promotes phospha-Michael addition reaction of trialkylphosphites to in situ generated ortho-quinone methides (o-QMs) for t
