Literature DB >> 32059062

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Shekhar Kc1, Roshan K Dhungana2, Namrata Khanal1, Ramesh Giri2.   

Abstract

We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary, and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary, and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aryltetralones; diarylcarbonyl compounds; dicarbofunctionalization; nickel catalysis; vinylarenes

Mesh:

Substances:

Year:  2020        PMID: 32059062      PMCID: PMC7274890          DOI: 10.1002/anie.201913435

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


  53 in total

1.  Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors:  Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal:  Science       Date:  2016-01-01       Impact factor: 47.728

2.  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

3.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

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.  Palladium-catalyzed 1,1-difunctionalization of ethylene.

Authors:  Vaneet Saini; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-10       Impact factor: 15.419

6.  Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation.

Authors:  Qiao Sun; Naohiko Yoshikai
Journal:  Org Lett       Date:  2019-06-20       Impact factor: 6.005

7.  Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts toward indanones and related compounds.

Authors:  Yongtao Chen; Chenyun Shu; Fang Luo; Xiaohui Xiao; Gangguo Zhu
Journal:  Chem Commun (Camb)       Date:  2018-05-22       Impact factor: 6.222

8.  Cobalt-catalyzed three-component coupling reaction of alkyl halides, 1,3-dienes, and trimethylsilylmethylmagnesium chloride.

Authors:  Keiya Mizutani; Hiroshi Shinokubo; Koichiro Oshima
Journal:  Org Lett       Date:  2003-10-16       Impact factor: 6.005

9.  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

10.  Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

Authors:  Xian Zhao; Hai-Yong Tu; Lei Guo; Shengqing Zhu; Feng-Ling Qing; Lingling Chu
Journal:  Nat Commun       Date:  2018-08-28       Impact factor: 14.919

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  9 in total

1.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

2.  Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2 *.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

3.  Three-Component Ni-Catalyzed Silylacylation of Alkenes.

Authors:  Dongshun Ni; M Kevin Brown
Journal:  ACS Catal       Date:  2021-01-26       Impact factor: 13.700

4.  Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp3)-C(sp3) Bonds.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2020-12-03       Impact factor: 15.419

5.  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

6.  Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents.

Authors:  Lei Liu; Wes Lee; Cassandra R Youshaw; Mingbin Yuan; Michael B Geherty; Peter Y Zavalij; Osvaldo Gutierrez
Journal:  Chem Sci       Date:  2020-07-24       Impact factor: 9.825

Review 7.  Walking metals: catalytic difunctionalization of alkenes at nonclassical sites.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Doleshwar Niroula; Ramesh Giri
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

8.  Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes.

Authors:  Xinyi Cheng; Xingchen Liu; Shengchun Wang; Ying Hu; Binjing Hu; Aiwen Lei; Jie Li
Journal:  Nat Commun       Date:  2021-07-16       Impact factor: 14.919

9.  Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles via radical/polar crossover.

Authors:  María Jesús Cabrera-Afonso; Anasheh Sookezian; Shorouk O Badir; Mirna El Khatib; Gary A Molander
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.969

  9 in total

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