Literature DB >> 32457562

Visible-Light-Induced Dearomatizations.

Mikiko Okumura1, David Sarlah1.   

Abstract

The dearomatization of aromatic compounds is an important synthetic strategy used in accessing complex three-dimensional structures from simple aromatic precursors. This minireview aims to provide an overview of recent advancements in this area, with a specific focus on visible-light-mediated dearomative transformations. Compared to the conventional high-energy ultraviolet (UV) light-promoted processes, not only these new approaches offer milder reaction conditions to accommodate wider variety of substrates with sensitive functionalities, but also enable the use of photocatalysts and other promoters, significantly expanding the reaction space. Application of these transformations to the synthesis of bioactive compounds are also discussed.

Entities:  

Keywords:  arene; dearomatization; functionalization; photochemistry; visible light

Year:  2019        PMID: 32457562      PMCID: PMC7250370          DOI: 10.1002/ejoc.201901229

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  37 in total

1.  Synthesis of gem-Difluorinated Spiro-γ-lactam Oxindoles by Visible-Light-Induced Consecutive Difluoromethylative Dearomatization, Hydroxylation, and Oxidation.

Authors:  Qiang Wang; Yi Qu; Qing Xia; Hongjian Song; Haibin Song; Yuxiu Liu; Qingmin Wang
Journal:  Chemistry       Date:  2018-07-09       Impact factor: 5.236

2.  Arenophile-Mediated Dearomative Reduction.

Authors:  Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-23       Impact factor: 15.336

3.  Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: efficient construction of 2-azaspiro[4.5]decanes.

Authors:  Bei Hu; Yuyuan Li; Wuheng Dong; Kai Ren; Xiaomin Xie; Jun Wan; Zhaoguo Zhang
Journal:  Chem Commun (Camb)       Date:  2016-03-04       Impact factor: 6.222

4.  Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

Authors:  Conghui Tang; Mikiko Okumura; Yunbo Zhu; Annie R Hooper; Yu Zhou; Yu-Hsuan Lee; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

Review 5.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

6.  Visible-Light-Induced Intermolecular Dearomative Cyclization of Furans: Synthesis of 1-Oxaspiro[4.4]nona-3,6-dien-2-one.

Authors:  Wuheng Dong; Yao Yuan; Xiaoshuang Gao; Miladili Keranmu; Wanfang Li; Xiaomin Xie; Zhaoguo Zhang
Journal:  J Org Chem       Date:  2019-01-11       Impact factor: 4.354

7.  Dearomative dihydroxylation with arenophiles.

Authors:  Emma H Southgate; Jola Pospech; Junkai Fu; Daniel R Holycross; David Sarlah
Journal:  Nat Chem       Date:  2016-08-22       Impact factor: 24.427

8.  Visible-Light-Promoted Dearomative Fluoroalkylation of β-Naphthols through Intermolecular Charge Transfer.

Authors:  Quanping Guo; Mengran Wang; Hong Liu; Rui Wang; Zhaoqing Xu
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-25       Impact factor: 15.336

9.  Functionalized spirolactones by photoinduced dearomatization of biaryl compounds.

Authors:  Hongji Li; Elena Subbotina; Anon Bunrit; Feng Wang; Joseph S M Samec
Journal:  Chem Sci       Date:  2019-02-19       Impact factor: 9.825

10.  Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes.

Authors:  Simone Stegbauer; Christian Jandl; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-05       Impact factor: 15.336

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  4 in total

1.  Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors:  Christopher J Huck; David Sarlah
Journal:  Chem       Date:  2020-07-01       Impact factor: 22.804

Review 2.  Advances in Catalytic Asymmetric Dearomatization.

Authors:  Chao Zheng; Shu-Li You
Journal:  ACS Cent Sci       Date:  2021-02-22       Impact factor: 14.553

3.  Dearomatization through Photoredox Hydroarylation: Discovery of a Radical-Polar Crossover Strategy.

Authors:  Kelly A McDaniel; Nathan T Jui
Journal:  Org Lett       Date:  2021-07-07       Impact factor: 6.072

4.  A visible-light Paternò-Büchi dearomatisation process towards the construction of oxeto-indolinic polycycles.

Authors:  Javier Mateos; Alberto Vega-Peñaloza; Pietro Franceschi; Francesco Rigodanza; Philip Andreetta; Xavier Companyó; Giorgio Pelosi; Marcella Bonchio; Luca Dell'Amico
Journal:  Chem Sci       Date:  2020-04-16       Impact factor: 9.825

  4 in total

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