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Literature DB >> 28474858

Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives.

Leifeng Wang¹, Fengjin Wu¹, Jiean Chen¹, David A Nicewicz^1,2, Yong Huang¹.

Abstract

We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.

Entities: Chemical

Keywords: cycloaddition; organocatalysis; photoredox chemistry; radical reactions; tetralin

Year: 2017 PMID： 28474858 DOI： 10.1002/anie.201702940

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

11 in total

1. Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors: Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal: J Am Chem Soc Date: 2018-01-10 Impact factor: 15.419

2. Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH₂ CH₂ ] → [CF₂ CHF] Isosterism.

Authors: Jessica Neufeld; Timo Stünkel; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Ryan Gilmour
Journal: Angew Chem Int Ed Engl Date: 2021-05-01 Impact factor: 15.336

Review 3. An overview on disulfide-catalyzed and -cocatalyzed photoreactions.

Authors: Yeersen Patehebieke
Journal: Beilstein J Org Chem Date: 2020-06-23 Impact factor: 2.883

4. Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C-H activation.

Authors: Mrinmoy Das; Minh Duy Vu; Qi Zhang; Xue-Wei Liu
Journal: Chem Sci Date: 2018-12-04 Impact factor: 9.825

5. Visible light enabled [4+2] annulation reactions for anthracenone-furans from 2,3-dibromonaphthoquinone and phenylbenzofurans.

Authors: Zhimei Mao; Aimin Huang; Lin Ma; Min Zhang
Journal: RSC Adv Date: 2021-11-29 Impact factor: 4.036

Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives.

1. Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

2. Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH₂ CH₂ ] → [CF₂ CHF] Isosterism.

Review 3. An overview on disulfide-catalyzed and -cocatalyzed photoreactions.

4. Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C-H activation.

5. Visible light enabled [4+2] annulation reactions for anthracenone-furans from 2,3-dibromonaphthoquinone and phenylbenzofurans.

6. Taming the radical cation intermediate enabled one-step access to structurally diverse lignans.

7. Bicyclo[2.2.0]hexene derivatives as a proaromatic platform for group transfer and chemical sensing.

Review 8. Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.

9. Oxidative [4+2] annulation of styrenes with alkynes under external-oxidant-free conditions.

10. Direct Synthesis of Bicyclic Acetals via Visible Light Catalysis.