741-74-2Relevant academic research and scientific papers
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
Benzylation of Arenes with Benzyl Halides under Promoter-Free and Additive-Free Conditions
Cheng, Xinqiang,Shan, Jiankai,Tian, Xinshe,Ren, Yun-Lai,Zhu, Yanyan
supporting information, p. 4404 - 4410 (2019/07/03)
It was found that benzyl chlorides and bromides could directly react with electron-rich arenes, which provided an example of promoter-free and additive-free benzylation of arenes. A variety of benzyl chlorides and bromides were treated with benzene rings to give the targeted products in low to high yields. The present conditions tolerated the vinyl group of the substrates. Preliminary mechanistic investigation suggests that the present reactions possibly proceed via an autocatalytic mechanism pathway.
Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes
Rao, H. Surya Prakash,Rao, A. Veera Bhadra
supporting information, p. 496 - 504 (2016/04/05)
A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a highyielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.
LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature
Ji, Xinfei,Huang, Tao,Wu, Wei,Liang, Fang,Cao, Song
supporting information, p. 5096 - 5099 (2015/11/03)
A practical and convenient approach for the secondary C(sp3)-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.
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.
Microwave-accelerated alkylation of arenes/heteroarenes with benzylic alcohols using antimony(III) chloride as catalyst: Synthesis of O-heterocycles
Shukla, Prashant,Choudhary, Manoj K.,Nayak, Sandip K.
supporting information; experimental part, p. 1585 - 1591 (2011/08/03)
An efficient protocol for alkylation of electron-rich arenes/heteroarenes with benzylic alcohols under microwave irradiation using antimony(III) chloride as catalyst has been developed. The mild reaction conditions, high yields, operational simplicity, and applicability to various substrates render the approach a useful route for the synthesis of diaryl/triarylalkane. In addition, a new route for the conversion of ortho-alkenylated phenols into functionalized O-heterocycles has been accomplished. Georg Thieme Verlag Stuttgart ? New York.
Friedel-Crafts Reaction with Arylcarbinols : One-Pot Synthesis of 10-Methylbenzo[a]fluoranthene
Talapatra, Bani,Chakraborty, Syamal,Biswas, Kallolmay,Mondal, Sudipta,Talapatra, Sunil Kumar
, p. 788 - 794 (2007/10/03)
Friedel-Crafts reaction with some monoaryl and diaryl carbinols have been studied. The products suggest a rational mode of formation of trityl alcohol and anthracene derivatives modifying the earlier reported conjecture of their formation from carbon monoxide, generated from benzhydrol and solvent benzene. It now appears that during Friedel-Crafts reaction the benzyl carbocation generated from benzhydrol may be arylated to triphenylmethane derivative. The latter under the experimental condition forms trityl cation which abstracts the hydroxyl group from the benzhydrol to form benzyl carbocation and trityl alcohol. Benzyl carbocations act both as a nucleophile and an eletrophile and dimerize to form anthracene derivatives. Incidentally, a one-pot synthesis of 10-methylbenzo[a]fluoranthene (26), characterized by NOE, decoupling and mass spectral studies, has been achieved in good yield by the Friedel-Crafts reaction of 9-fluourenol, thus providing a simple method of its synthesis.
