Literature DB >> 31390474

Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Matteo Chierchia1, Peilin Xu1, Gabriel J Lovinger1, James P Morken1.   

Abstract

A hybrid transition-metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; catalysis; cross-coupling; nickel; radical reactions

Mesh：

Substances：

Year:  2019        PMID： 31390474      PMCID： PMC6764867          DOI： 10.1002/anie.201908029

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


  71 in total

1.  Cobalt-catalyzed tandem radical cyclization and cross-coupling reaction: its application to benzyl-substituted heterocycles.

Authors:  K Wakabayashi; H Yorimitsu; K Oshima
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides.

Authors:  Arkady Krasovskiy; Vladimir Malakhov; Andrei Gavryushin; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

3.  Bond formations between two nucleophiles: transition metal catalyzed oxidative cross-coupling reactions.

Authors:  Chao Liu; Hua Zhang; Wei Shi; Aiwen Lei
Journal:  Chem Rev       Date:  2011-02-23       Impact factor: 60.622

4.  Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

Authors:  Xiaolong Yu; Tao Yang; Shulin Wang; Hailiang Xu; Hegui Gong
Journal:  Org Lett       Date:  2011-03-24       Impact factor: 6.005

5.  Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.

Authors:  Yoshizumi Yasui; Haruhi Kamisaki; Yoshiji Takemoto
Journal:  Org Lett       Date:  2008-06-27       Impact factor: 6.005

6.  Palladium-catalyzed homocoupling reactions between two Csp(3)-Csp(3) centers.

Authors:  Aiwen Lei; Xumu Zhang
Journal:  Org Lett       Date:  2002-07-11       Impact factor: 6.005

7.  Ni-catalyzed cascade formation of C(sp3)--C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides.

Authors:  Vilas B Phapale; Elena Buñuel; Miguel García-Iglesias; Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Mechanistic approaches to palladium-catalyzed alkene difunctionalization reactions.

Authors:  Katrina H Jensen; Matthew S Sigman
Journal:  Org Biomol Chem       Date:  2008-10-09       Impact factor: 3.876

9.  What is the rate of the Csp2-Csp2 reductive elimination step? Revealing an unusually fast Ni-catalyzed Negishi-type oxidative coupling reaction.

Authors:  Liqun Jin; Hua Zhang; Peng Li; John R Sowa; Aiwen Lei
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  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
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  12 in total

1.  Recent Advances in Radical Addition to Alkenylboron Compounds.

Authors:  Gabriel J Lovinger; James P Morken
Journal:  European J Org Chem       Date:  2019-11-21

2.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

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

3.  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

4.  Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.

Authors:  Mark W Campbell; Mingbin Yuan; Viktor C Polites; Osvaldo Gutierrez; Gary A Molander
Journal:  J Am Chem Soc       Date:  2021-03-04       Impact factor: 15.419

5.  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

6.  Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.

Authors:  Chenlong Zhang; Weipeng Hu; Gabriel J Lovinger; Jing Jin; Jingjia Chen; James P Morken
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

7.  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

8.  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

9.  Nickel-catalyzed three-component olefin reductive dicarbofunctionalization to access alkylborates.

Authors:  Xiao-Xu Wang; Xi Lu; Shi-Jiang He; Yao Fu
Journal:  Chem Sci       Date:  2020-07-08       Impact factor: 9.825

10.  Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.

Authors:  Roshan K Dhungana; Vivek Aryal; Doleshwar Niroula; Rishi R Sapkota; Margaret G Lakomy; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823
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