Literature DB >> 30672703

Mechanism and Regioselectivity of an Unsymmetrical Hexadehydro-Diels-Alder (HDDA) Reaction.

Maggie Chen1, Cyndi Qixin He1, K N Houk1.   

Abstract

Hoye reported intramolecular hexadehydro-Diels-Alder (HDDA) reactions to generate arynes that functionalize natural product phenols and amines. In their studies, Hoye found that unsymmetrical tetraynes selectively form a single aryne. We report density functional theory (DFT) calculations that reveal the factors controlling the regioselectivity.

Entities:  

Year:  2019        PMID： 30672703     DOI： 10.1021/acs.joc.8b02865

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.

Authors:  Xiao Xiao; Thomas R Hoye
Journal:  J Am Chem Soc       Date:  2019-06-14       Impact factor: 15.419

2.  Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr').

Authors:  Sahil Arora; Dorian S Sneddon; Thomas R Hoye
Journal:  European J Org Chem       Date:  2020-02-13

3.  "Kobayashi Benzynes" as Hexadehydro-Diels-Alder Diynophiles.

Authors:  Sahil Arora; Thomas R Hoye
Journal:  Org Lett       Date:  2021-04-22       Impact factor: 6.005

4.  Arylhydrazine Trapping of Benzynes: Mechanistic Insights and a Route to Azoarenes.

Authors:  Dorian S Sneddon; Thomas R Hoye
Journal:  Org Lett       Date:  2021-04-19       Impact factor: 6.005

Review 5.  Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.

Authors:  Lucas L Fluegel; Thomas R Hoye
Journal:  Chem Rev       Date:  2021-01-25       Impact factor: 60.622
  5 in total

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