Literature DB >> 26655335

Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and Aldehydes via Aryl-Aryl Amino Group Migration.

Sachin Suresh Bhojgude1, Dnyaneshwar R Baviskar1, Rajesh G Gonnade1, Akkattu T Biju1.   

Abstract

The transition-metal-free multicomponent coupling of arynes, aromatic tertiary amines, and aldehydes proceeding via the aryl to aryl amino group migration has been demonstrated. This protocol allows rapid access to ortho-functionalized tertiary amines in moderate to good yields. Moreover, activated ketones can also be used as the aldehyde component in the present reaction. The similarity of the aryl-aryl tertiary amino group migration with the Smiles rearrangement is striking.

Entities:  

Year:  2015        PMID: 26655335     DOI: 10.1021/acs.orglett.5b03319

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes.

Authors:  Jiupeng Liu; Shuo Tang; Mengyao Zhao; Jianing Huai; Jingya Yu; Jingjing Zhao; Pan Li
Journal:  ACS Omega       Date:  2021-12-15

2.  Expanding the synthesizable multisubstituted benzo[b]thiophenes via 6,7-thienobenzynes generated from o-silylaryl triflate-type precursors.

Authors:  Suguru Yoshida; Tomoko Kuribara; Takamoto Morita; Tsubasa Matsuzawa; Kazushi Morimoto; Takuya Kobayashi; Takamitsu Hosoya
Journal:  RSC Adv       Date:  2018-06-13       Impact factor: 3.361

  2 in total

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