Literature DB >> 23957502

Reaction of arynes with vinylogous amides: nucleophilic addition to the ortho-quinodimethide intermediate.

Ran Li1, Xuemei Wang, Zhibin Wei, Chunrui Wu, Feng Shi.   

Abstract

The reaction of arynes with vinylogous amides containing no free N-H bonds proceeds in a [2 + 2] cycloaddition fashion at ambient temperature. The electronic properties of the vinylogous amides allow for the cycloadducts undergoing a facile ring-opening process, leading to electronically biased ortho-quinodimethide intermediates. Subsequent nucleophilic addition with alcohols affords 2-substituted benzaldehydes or ketones.

Entities:  

Mesh:

Substances:

Year:  2013        PMID: 23957502     DOI: 10.1021/ol4018968

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


  3 in total

1.  Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

Authors:  Eito Yoshioka; Shigeru Kohtani; Hideto Miyabe
Journal:  Molecules       Date:  2014-01-13       Impact factor: 4.411

Review 2.  Transition-Metal-Free Activation of Amide Bond by Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2018-08-27       Impact factor: 4.411

Review 3.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.