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The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.
Org Lett. 2016 11 04; 18(21):5596-5599.OL

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.

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Authors+Show Affiliations

Zhang J
Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
Niu D
Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
Brinker VA
Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
Hoye TR
Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.

MeSH

AlkynesBenzene DerivativesCycloaddition ReactionMolecular ConformationPhenolsQuantum TheoryStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27767316

Citation

Zhang, Juntian, et al. "The Phenol-Ene Reaction: Biaryl Synthesis Via Trapping Reactions Between HDDA-Generated Benzynes and Phenolics." Organic Letters, vol. 18, no. 21, 2016, pp. 5596-5599.
Zhang J, Niu D, Brinker VA, et al. The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics. Org Lett. 2016;18(21):5596-5599.
Zhang, J., Niu, D., Brinker, V. A., & Hoye, T. R. (2016). The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics. Organic Letters, 18(21), 5596-5599.
Zhang J, et al. The Phenol-Ene Reaction: Biaryl Synthesis Via Trapping Reactions Between HDDA-Generated Benzynes and Phenolics. Org Lett. 2016 11 4;18(21):5596-5599. PubMed PMID: 27767316.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics. AU - Zhang,Juntian, AU - Niu,Dawen, AU - Brinker,Vincent A, AU - Hoye,Thomas R, Y1 - 2016/10/21/ PY - 2016/11/5/pubmed PY - 2018/6/27/medline PY - 2016/11/5/entrez SP - 5596 EP - 5599 JF - Organic letters JO - Org Lett VL - 18 IS - 21 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/27767316/The_Phenol_Ene_Reaction:_Biaryl_Synthesis_via_Trapping_Reactions_between_HDDA_Generated_Benzynes_and_Phenolics_ DB - PRIME DP - Unbound Medicine ER -