Literature DB >> 20361749

Sequential reaction of arynes via insertion into the pi-bond of amides and trapping reaction with dialkylzincs.

Eito Yoshioka1, Shigeru Kohtani, Hideto Miyabe.   

Abstract

The sequential transformation of arynes into ortho-disubstituted arenes is achieved by a one-pot procedure using formamides and dialkylzincs. This reaction proceeded via a route involving the trapping reaction of the formal [2 + 2] cycloaddition adducts or quinone methides generated by the insertion of arynes into the C=O bond of amides.

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Year:  2010        PMID: 20361749     DOI: 10.1021/ol100387h

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


  5 in total

1.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

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

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

Review 4.  Benzoxetes and benzothietes--heterocyclic analogues of benzocyclobutene.

Authors:  Herbert Meier
Journal:  Molecules       Date:  2012-02-07       Impact factor: 4.411

Review 5.  Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2015-07-09       Impact factor: 4.411

  5 in total

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