80335-44-0Relevant academic research and scientific papers
1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines
Cho, Seoyoung,Wang, Qiu
supporting information, (2020/02/28)
ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation of various functionalities such as amine, azide, oxygen, sulfur, halide, alkynyl, aryl, vinyl, and alkyl groups in a modular manner for the synthesis of diverse aniline skeletons.
Three-Component Aminoselenation of Arynes
Gaykar, Rahul N.,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
supporting information, p. 9613 - 9617 (2019/11/28)
The three-component coupling of tertiary amines, arynes, and aryl selenium bromide or diaryl diselenide as an electrophilic selenium source allowing the synthesis of 2-selanyl aniline derivatives is reported. This aminoselenation reaction of arynes installs a C-N and C-Se bond under mild conditions, and the products are formed in moderate to good yields. This reaction is compatible with various functional groups, and the preliminary studies on the mechanism of the reaction is also provided.
Transition-Metal-Free Thioamination of Arynes Using Sulfenamides
Gaykar, Rahul N.,Bhattacharjee, Subrata,Biju, Akkattu T.
, p. 737 - 740 (2019/01/25)
The insertion of arynes into the S-N σ-bond of sulfenamides allowing the synthesis of o-sulfanylaniline derivatives with reasonable functional group compatibility is presented. The aryne generated from 2-(trimethylsilyl)aryl triflates using CsF in DME was the key for the success of this transition-metal-free thioamination reaction, which involves new C-N and C-S bond formations in a single step under mild conditions. Moreover, the synthetic potential of this method was demonstrated by the synthesis of the antidepressant drug vortioxetine.
Double heteroatom functionalization of arenes using benzyne three-component coupling
Garca-Lpez, Jos-Antonio,etin, Meliha,Greaney, Michael F.
supporting information, p. 2156 - 2159 (2015/02/19)
Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2- difunctionalized arenes.
REACTION OF BENZOTHIAZOLINE WITH BENZYNE - GENERATION OF NOVEL HETEROCYCLIC SULFUR YLIDE, BENZOTHIAZOLINIUM S-YLIDE
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Ueda, Norihiro
, p. 3071 - 3074 (2007/10/02)
A novel heterocyclic sulfur ylide, 2-t-butyl-3-methyl-1-phenylbenzothiazolinium ylide (13) was generated as an intermediate in the reaction of 2-t-butyl-3-methylbenzothiazoline (2) with benzyne.The S-ylide 13 underwent a novel intermolecular shift to give 2-t-butyl-3-methyl-2-phenylbenzothiazoline .
