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Literature DB >> 27767316

The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.

Juntian Zhang¹, Dawen Niu¹, Vincent A Brinker¹, Thomas R Hoye¹.

Abstract

Benzynes produced thermally by the cycloisomerization of triyne-containing precursors [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with phenols at the carbon ortho to the hydroxyl in an enelike fashion. Following tautomerization of the intermediate cyclohexadienones, this produces biaryl derivatives. DFT calculations of model reactions support this mechanistic interpretation. Substituted, unsymmetrical phenols and bis-phenols react in a fashion that can be explained by engagement of the most readily available (non-hydrogen-bonded) hydroxyl in the phenol-ene process.

Entities: Chemical Disease Gene Species

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Year: 2016 PMID： 27767316 PMCID： PMC5107112 DOI： 10.1021/acs.orglett.6b02830

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

13 in total

1. Facile O-arylation of phenols and carboxylic acids.

Authors: Zhijian Liu; Richard C Larock
Journal: Org Lett Date: 2004-01-08 Impact factor: 6.005

2. Transition-metal-free direct arylation of anilines.

Authors: Tracey Pirali; Fengzhi Zhang; Anna H Miller; Jenna L Head; Donald McAusland; Michael F Greaney
Journal: Angew Chem Int Ed Engl Date: 2011-12-12 Impact factor: 15.336

3. Alder-ene reactions of arynes.

Authors: Rajdip Karmakar; Phani Mamidipalli; Sang Young Yun; Daesung Lee
Journal: Org Lett Date: 2013-03-29 Impact factor: 6.005

4. Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

Authors: Thanh Truong; Olafs Daugulis
Journal: Chem Sci Date: 2013 Impact factor: 9.825

Review 5. Thiol-ene click chemistry.

Authors: Charles E Hoyle; Christopher N Bowman
Journal: Angew Chem Int Ed Engl Date: 2010-02-22 Impact factor: 15.336

6. Employing Arynes in Diels-Alder Reactions and Transition-Metal-Free Multicomponent Coupling and Arylation Reactions.

Authors: Sachin Suresh Bhojgude; Anup Bhunia; Akkattu T Biju
Journal: Acc Chem Res Date: 2016-08-25 Impact factor: 22.384

7. Indolyne and aryne distortions and nucleophilic regioselectivites.

Authors: Paul H-Y Cheong; Robert S Paton; Sarah M Bronner; G-Yoon J Im; Neil K Garg; K N Houk
Journal: J Am Chem Soc Date: 2010-02-03 Impact factor: 15.419

8. Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring.

Authors: Toshiyuki Hamura; Yousuke Ibusuki; Kazuhiko Sato; Takashi Matsumoto; Yoshihiro Osamura; Keisuke Suzuki
Journal: Org Lett Date: 2003-10-02 Impact factor: 6.005

9. The aromatic ene reaction.

Authors: Dawen Niu; Thomas R Hoye
Journal: Nat Chem Date: 2013-11-17 Impact factor: 24.427

10. The hexadehydro-Diels-Alder reaction.

Authors: Thomas R Hoye; Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods
Journal: Nature Date: 2012-10-11 Impact factor: 49.962

9 in total

1. Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations.

Authors: Juntian Zhang; Thomas R Hoye
Journal: Org Lett Date: 2019-04-10 Impact factor: 6.005

2. Cu^I -Mediated Bromoalkynylation and Hydroalkynylation Reactions of Unsymmetrical Benzynes: Complementary Modes of Addition.

Authors: Xiao Xiao; Tao Wang; Feng Xu; Thomas R Hoye
Journal: Angew Chem Int Ed Engl Date: 2018-11-15 Impact factor: 15.336

The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.

1. Facile O-arylation of phenols and carboxylic acids.

2. Transition-metal-free direct arylation of anilines.

3. Alder-ene reactions of arynes.

4. Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

Review 5. Thiol-ene click chemistry.

6. Employing Arynes in Diels-Alder Reactions and Transition-Metal-Free Multicomponent Coupling and Arylation Reactions.

7. Indolyne and aryne distortions and nucleophilic regioselectivites.

8. Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring.

9. The aromatic ene reaction.

10. The hexadehydro-Diels-Alder reaction.

1. Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations.

2. Cu^I -Mediated Bromoalkynylation and Hydroalkynylation Reactions of Unsymmetrical Benzynes: Complementary Modes of Addition.

3. Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.

4. Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.

5. The Aza-hexadehydro-Diels-Alder Reaction.

6. Mechanistic Duality in Tertiary Amine Additions to Thermally Generated Hexadehydro-Diels-Alder Benzynes.

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

Review 8. Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.

9. Reactions of thermally generated benzynes with six-membered N-heteroaromatics: pathway and product diversity.