Literature DB >> 34334831

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

Xuchen Zhao1, Jon D Rainier1.   

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.

Entities:  

Keywords:  aromaticity; cross-coupling; dihydrophenanthrene; electrocyclization; natural product synthesis; photochemistry; singlet-excited state; triplet-excited state

Year:  2021        PMID： 34334831      PMCID： PMC8319837          DOI： 10.1055/s-0040-1706001

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  19 in total

1.  Control of kinetics and thermodynamics of [1,5]-shifts by aromaticity: a view through the prism of Marcus theory.

Authors:  Igor V Alabugin; Mariappan Manoharan; Boris Breiner; Frederick D Lewis
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

Review 2.  Natural phenanthrenes and their biological activity.

Authors:  Adriána Kovács; Andrea Vasas; Judit Hohmann
Journal:  Phytochemistry       Date:  2008-02-19       Impact factor: 4.072

3.  Controlled iterative cross-coupling: on the way to the automation of organic synthesis.

Authors:  Congyang Wang; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Vinyl nosylates: an ideal partner for palladium-catalyzed cross-coupling reactions.

Authors:  Nicolas P Cheval; Anna Dikova; Aurélien Blanc; Jean-Marc Weibel; Patrick Pale
Journal:  Chemistry       Date:  2013-05-21       Impact factor: 5.236

5.  Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.

Authors:  David L Sloman; Branko Mitasev; Stephen S Scully; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-18       Impact factor: 15.336

6.  Symmetry-enforced conformational control of photochemical reactivity in 2-vinyl-1,3-terphenyl.

Authors:  Frederick D Lewis; Xiaobing Zuo; Vladimir Gevorgyan; Michael Rubin
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

7.  Silver-catalyzed arylation of (hetero)arenes by oxidative decarboxylation of aromatic carboxylic acids.

Authors:  Jian Kan; Shijun Huang; Jin Lin; Min Zhang; Weiping Su
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-23       Impact factor: 15.336

8.  Photoelectrocyclization Reactions of Conjugated Cycloalkenones: Scope and Reactivity.

Authors:  Xuchen Zhao; Changqing Song; Jon D Rainier
Journal:  J Org Chem       Date:  2020-04-01       Impact factor: 4.354

9.  Conformer-specific photoisomerizaton of some 2-vinylbiphenyls.

Authors:  Frederick D Lewis; Xiaobing Zuo
Journal:  Photochem Photobiol Sci       Date:  2003-11       Impact factor: 3.982

10.  Stereodivergent Photoelectrocyclization Reactions of Bis-aryl Cycloalkenones: Intercepting Photoelectrocyclization Intermediates with Acid.

Authors:  Xuchen Zhao; Changqing Song; Jon D Rainier
Journal:  Org Lett       Date:  2019-10-17       Impact factor: 6.005
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  1 in total

1.  Biphenyl Cyclobutenone Photoelectrocyclizations.

Authors:  Changhang Dai; Xuchen Zhao; Changqing Song; Zach Schwartz; Jon D Rainier
Journal:  J Org Chem       Date:  2021-09-29       Impact factor: 4.354
  1 in total

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