102751-83-7Relevant articles and documents
The role of charge in 1,2,3-triazol(ium)-based halogen bonding activators
Dreger, Alexander,Engelage, Elric,Mallick, Bert,Beer, Paul D.,Huber, Stefan M.
, p. 4013 - 4016 (2018)
The influence of charge on the performance of monocationic and dicationic triazol(ium)-based halogen bond donors was investigated. Next to the activity in a halide abstraction benchmark reaction, halogen bonding was also evaluated via X-ray structural analyses and isothermal titration calorimetry.
Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution
Voelkel, Martin H. H.,Wonner, Patrick,Huber, Stefan Matthias
, p. 214 - 224 (2020)
Preorganization is a powerful tool in supramolecular chemistry which has been utilized successfully in intra- and intermolecular halogen bonding. In previous work, we had developed a bidentate bis(iodobenzimidazolium)-based halogen bond donor which featured a central trifluoromethyl substituent. This compound showed a markedly increased catalytic activity compared to unsubstituted bis(iodoimidazolium)-based Lewis acids, which could be explained either by electronic effects (the electron withdrawal by the fluorinated substituent) or by preorganization (the hindered rotation of the halogen bonding moieties). Herein, we systematically investigate the origin of this increased Lewis acidity via a comparison of the two types of compounds and their respective derivatives with or without the central trifluoromethyl group. Calorimetric measurements of halide complexations indicated that preorganization is the main reason for the higher halogen bonding strength. The performance of the catalysts in a series of benchmark reactions corroborates this finding.
Tritylium assisted iodine catalysis for the synthesis of unsymmetrical triarylmethanes
Boyarskaya, Dina V.,Courant, Thibaut,Lombard, Marine,Masson, Géraldine,Neuville, Luc
supporting information, p. 6502 - 6508 (2020/09/09)
The combined Lewis acid catalytic system, generated from molecular iodine and tritylium tetrafluoroborate effectively catalyzed the Friedel-Crafts (FC) arylation of diarylmethyl sulfides providing an efficient access to various unsymmetrical triarylmethanes. The addition of tritylium and iodine created a more active catalytic system to promote the cleavage of sulfidic C-S bonds. This journal is
Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
Lanzi, Matteo,Merad, Jérémy,Boyarskaya, Dina V.,Maestri, Giovanni,Allain, Clémence,Masson, Géraldine
supporting information, p. 5247 - 5250 (2018/09/13)
The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.
Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
Nambo, Masakazu,Ariki, Zachary T.,Canseco-Gonzalez, Daniel,Beattie, D. Dawson,Crudden, Cathleen M.
, p. 2339 - 2342 (2016/06/09)
A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
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
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.
Organocatalyzed Friedel-Crafts arylation of benzylic alcohols
McCubbin, J. Adam,Krokhin, Oleg V.
supporting information; experimental part, p. 2447 - 2449 (2010/07/04)
Electron-rich aromatic and heteroaromatic rings are functionalized directly with a variety of benzylic alcohols under mild conditions. The reaction is catalyzed by commercially available pentafluorophenylboronic acid, which is stable under ambient conditions and recoverable. The reaction itself is highly atom economical and produces water as the only byproduct. A Friedel-Crafts mechanism is proposed.
Direct benzylation and allylic alkylation in high-temperature water without added catalysts
Hirashita, Tsunehisa,Kuwahara, Sho,Okochi, Sota,Tsuji, Makoto,Araki, Shuki
experimental part, p. 1847 - 1851 (2010/09/07)
In high-temperature water a series of benzyl and allylic alcohols reacted with 1,3-dicarbonyl compounds and activated aromatic compounds to give the alkylated products without added catalysts.
