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The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions Towards Phenanthrene Derivatives

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Publisher Thieme
Specialty Chemistry
Date 2021 Aug 2
PMID 34334831
Citations 3
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Abstract

The photoelectrocyclization of conjugated vinyl biaryls has proven to be a valuable and efficient strategy for generating phenanthrene derivatives. Contained in this review is an overview of the mechanism for the transformation and a discussion of the reaction scope with a focus on the electrocyclization itself, rearomatization, and the application of the reaction in natural product synthesis.

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References
1.
Kan J, Huang S, Lin J, Zhang M, Su W . Silver-catalyzed arylation of (hetero)arenes by oxidative decarboxylation of aromatic carboxylic acids. Angew Chem Int Ed Engl. 2014; 54(7):2199-203. DOI: 10.1002/anie.201408630. View

2.
Cheval N, Dikova A, Blanc A, Weibel J, Pale P . Vinyl nosylates: an ideal partner for palladium-catalyzed cross-coupling reactions. Chemistry. 2013; 19(27):8765-8. DOI: 10.1002/chem.201300127. View

3.
Lewis F, Zuo X . Conformer-specific photoisomerizaton of some 2-vinylbiphenyls. Photochem Photobiol Sci. 2003; 2(11):1059-66. DOI: 10.1039/b305831j. View

4.
Zhao X, Song C, Rainier J . Photoelectrocyclization Reactions of Conjugated Cycloalkenones: Scope and Reactivity. J Org Chem. 2020; 85(8):5449-5463. PMC: 7847264. DOI: 10.1021/acs.joc.0c00197. View

5.
Kovacs A, Vasas A, Hohmann J . Natural phenanthrenes and their biological activity. Phytochemistry. 2008; 69(5):1084-110. DOI: 10.1016/j.phytochem.2007.12.005. View