Literature DB >> 34045772

An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.

Doleshwar Niroula1, Rishi R Sapkota1, Roshan K Dhungana1, Bijay Shrestha1,2, Ramesh Giri1.   

Abstract

We report a nickel-catalyzed one pot synthesis of 9-arylmethylanthracene motifs, which find applications in medicinal and material chemistry. In this synthesis, we apply three component alkene dicarbofunctionalization of 2-vinylaldimines with aryl iodides and arylzinc reagent to generate a 1,1,2-diarylethyl scaffold, which then undergoes an acidpromoted cyclization followed by aromatization to furnish 9-arylmethylanthracene cores. With the new method, a number of differently-substituted 9-arylmethylanthracene derivatives can be synthesized in good yields.

Entities:  

Keywords:  Arylmethylanthracene; cyclization; dicarbofunctionalization; nickel-catalyzed; regioselective; vinylaldimines

Year:  2020        PMID: 34045772      PMCID: PMC8153705          DOI: 10.1002/ijch.201900158

Source DB:  PubMed          Journal:  Isr J Chem        ISSN: 0021-2148            Impact factor:   3.333


  30 in total

1.  Flexible and practical synthesis of anthracenes through gold-catalyzed cyclization of o-alkynyldiarylmethanes.

Authors:  Chao Shu; Cheng-Bin Chen; Wei-Xi Chen; Long-Wu Ye
Journal:  Org Lett       Date:  2013-10-24       Impact factor: 6.005

2.  Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles.

Authors:  Bijay Shrestha; Prakash Basnet; Roshan K Dhungana; Shekhar Kc; Surendra Thapa; Jeremiah M Sears; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2017-07-26       Impact factor: 15.419

3.  1,2-Diarylation of alkenes with aryldiazonium salts and arenes enabled by visible light photoredox catalysis.

Authors:  Xuan-Hui Ouyang; Jiang Cheng; Jin-Heng Li
Journal:  Chem Commun (Camb)       Date:  2018-07-20       Impact factor: 6.222

4.  Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes.

Authors:  Andrés García-Domínguez; Zhaodong Li; Cristina Nevado
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

5.  Anthracene-Based Receptors with a Turn-on Fluorescence Response for Nitrate.

Authors:  Siva S R Namashivaya; Aleksandr S Oshchepkov; Hui Ding; Sebastian Förster; Victor N Khrustalev; Evgeny A Kataev
Journal:  Org Lett       Date:  2019-10-11       Impact factor: 6.005

6.  Acid-catalyzed cyclization of anthracenol derivatives to homotriptycenes.

Authors:  Chunmei Gao; Derong Cao; Sheyang Xu; Herbert Meier
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

7.  Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes.

Authors:  Tatsuya Fukutani; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

8.  Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies.

Authors:  Shekhar Kc; Roshan K Dhungana; Bijay Shrestha; Surendra Thapa; Namrata Khanal; Prakash Basnet; Robert W Lebrun; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2018-07-30       Impact factor: 15.419

9.  Intermolecular dialkylation of alkenes with two distinct C(sp3)─H bonds enabled by synergistic photoredox catalysis and iron catalysis.

Authors:  Xuan-Hui Ouyang; Yang Li; Ren-Jie Song; Ming Hu; Shenglian Luo; Jin-Heng Li
Journal:  Sci Adv       Date:  2019-03-29       Impact factor: 14.136

10.  Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes.

Authors:  David Anthony; Qiao Lin; Judith Baudet; Tianning Diao
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-11       Impact factor: 15.336

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  2 in total

1.  Directing group assisted rhodium catalyzed meta-C-H alkynylation of arenes.

Authors:  Sheuli Sasmal; Gaurav Prakash; Uttam Dutta; Ranjini Laskar; Goutam Kumar Lahiri; Debabrata Maiti
Journal:  Chem Sci       Date:  2022-04-20       Impact factor: 9.969

2.  Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions.

Authors:  Laura M Wickham; Ramesh Giri
Journal:  Acc Chem Res       Date:  2021-08-12       Impact factor: 24.466

  2 in total

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