91132-57-9Relevant academic research and scientific papers
Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides
Zhong, Tao,Pang, Meng-Ke,Chen, Zhi-Da,Zhang, Bin,Weng, Jiang,Lu, Gui
supporting information, p. 3072 - 3078 (2020/04/10)
A copper-free Sandmeyer-type fluorosulfonylation reaction is reported. Utilizing Na2S2O5 and Selectfluor as the sulfur dioxide and fluorine sources, respectively, aryldiazonium salts were transformed into sulfonyl fluorides. The one-pot direct synthesis of sulfonyl fluorides from aromatic amines was also realized via in situ diazotization. The practicality of this method was demonstrated by the broad functional group tolerance, gram-scale synthesis, and late-stage fluorosulfonylation of natural products and pharmaceuticals.
Trifluoromethylation of arenediazonium salts with fluoroform-derived CuCF3 in aqueous media
Lishchynskyi, Anton,Berthon, Guillaume,Grushin, Vladimir V.
supporting information, p. 10237 - 10240 (2014/08/18)
A new protocol has been developed for trifluoromethylation of arenediazonium salts with moisture-sensitive CuCF3 (from fluoroform) in aqueous media. The reaction is governed by a radical mechanism, tolerates a broad variety of functional groups, and is applicable to the synthesis of complex, polyfunctionalized molecules. This journal is the Partner Organisations 2014.
Tailoring atropisomeric maleimides for stereospecific [2 + 2] photocycloaddition-photochemical and photophysical investigations leading to visible-light photocatalysis
Kumarasamy, Elango,Raghunathan, Ramya,Jockusch, Steffen,Ugrinov, Angel,Sivaguru
supporting information, p. 8729 - 8737 (2014/07/07)
Atropisomeric maleimides were synthesized and employed for stereospecific [2 + 2] photocycloaddition. Efficient reaction was observed under direct irradiation, triplet-sensitized UV irradiation, and non-metal catalyzed visible-light irradiation, leading to two regioisomeric (exo/endo) photoproducts with complete chemoselectivity (exclusive [2 + 2] photoproduct). High enantioselectivity (ee > 98%) and diastereoselectivity (dr > 99:1%) were observed under the employed reaction conditions and were largely dependent on the substituent on the maleimide double bond but minimally affected by the substituents on the alkenyl tether. On the basis of detailed photophysical studies, the triplet energies of the maleimides were estimated. The triplet lifetimes appeared to be relatively short at room temperature as a result of fast [2 + 2] photocycloaddition. For the visible-light mediated reaction, triplet energy transfer occurred with a rate constant close to the diffusion-limited value. The mechanism was established by generation of singlet oxygen from the excited maleimides. The high selectivity in the photoproduct upon reaction from the triplet excited state was rationalized on the basis of conformational factors as well as the type of diradical intermediate that was preferred during the photoreaction.
Arylative cyclization of 2-isocyanobiphenyls with anilines: One-pot synthesis of 6-arylphenanthridines via competitive reaction pathways
Xia, Zhonghua,Huang, Jinbo,He, Yimiao,Zhao, Jiaji,Lei, Jian,Zhu, Qiang
supporting information, p. 2546 - 2549 (2014/05/20)
A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.
Copper-promoted sandmeyer trifluoromethylation reaction
Dai, Jian-Jun,Fang, Chi,Xiao, Bin,Yi, Jun,Xu, Jun,Liu, Zhao-Jing,Lu, Xi,Liu, Lei,Fu, Yao
supporting information, p. 8436 - 8439 (2013/07/19)
A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.
The first intramolecular Heck-Matsuda reaction and its application in the syntheses of benzofurans and indoles
Siqueira, Fernanda A.,Taylor, Jason G.,Correia, Carlos Roque D.
supporting information; experimental part, p. 2102 - 2105 (2010/06/14)
In this Letter, we report, for the first time, the development of an efficient method for the intramolecular Heck reaction of arenediazonium salts in the synthesis of benzofuran and indole derivatives. In addition, this methodology allowed the synthesis of a series of dihydrobenzofuran acetic acid derivatives via a domino Heck-Matsuda coupling-carbonylation reaction.
Gas Phase Generation and Reactions of o-Dialkylaminobenyzl and o-Dialkylaminophenoxyl Radicals
Cadogan, J. I. G.,Hickson, Clare L.,Husband, James B.,McNab, Hamish
, p. 1891 - 1896 (2007/10/02)
Generation of the title radicals was effected by flash vacuum pyrolysis of benzyl phenyl ethers, and O-allyl ethers, respectively.The major products are formed by a multi-step sequence involving (i) intramolecular hydrogen transfer from the alkylamino group to the initial radical cemtre, (ii) rearrangement of the resulting aminoalkyl radical, (iii) expulsion of the nitrogen residue to give a bezyl radical which leads to products.
