Literature DB >> 32905517

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Kelsey E Poremba1, Sara E Dibrell1, Sarah E Reisman1.   

Abstract

Nickel-catalyzed reductive cross-coupling reactions have emerged as powerful methods to join two electrophiles. These reactions have proven particularly useful for the coupling of sec-alkyl electrophiles to form stereogenic centers; however, the development of enantioselective variants remains challenging. In this Perspective, we summarize the progress that has been made toward Ni-catalyzed enantioselective reductive cross-coupling reactions.

Entities:  

Year:  2020        PMID: 32905517      PMCID: PMC7470226          DOI: 10.1021/acscatal.0c01842

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  78 in total

1.  Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides.

Authors:  Mengyu Gao; Deli Sun; Hegui Gong
Journal:  Org Lett       Date:  2019-02-25       Impact factor: 6.005

2.  Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach.

Authors:  Cristofer Pezzetta; Davide Bonifazi; Robert W M Davidson
Journal:  Org Lett       Date:  2019-10-24       Impact factor: 6.005

3.  Nickel-catalyzed reductive coupling of aryl halides with secondary alkyl bromides and allylic acetate.

Authors:  Shulin Wang; Qun Qian; Hegui Gong
Journal:  Org Lett       Date:  2012-06-14       Impact factor: 6.005

4.  Reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl and heteroaryl bromides.

Authors:  Gary A Molander; Kaitlin M Traister; Brian T O'Neill
Journal:  J Org Chem       Date:  2014-06-03       Impact factor: 4.354

5.  Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides.

Authors:  Daniel A Everson; Ruja Shrestha; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2010-01-27       Impact factor: 15.419

Review 6.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

7.  Nickel/Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling of Racemic α-Chloro Esters with Aryl Iodides.

Authors:  Haixing Guan; Qianwen Zhang; Patrick J Walsh; Jianyou Mao
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-10       Impact factor: 15.336

8.  Enantioselective cross-coupling of meso-epoxides with aryl halides.

Authors:  Yang Zhao; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2015-03-02       Impact factor: 15.419

9.  Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation.

Authors:  Nathan D Schley; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

Review 10.  Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes.

Authors:  Gregory C Fu
Journal:  ACS Cent Sci       Date:  2017-06-12       Impact factor: 14.553

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  22 in total

1.  Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

Authors:  David J Charboneau; Haotian Huang; Emily L Barth; Cameron C Germe; Nilay Hazari; Brandon Q Mercado; Mycah R Uehling; Susan L Zultanski
Journal:  J Am Chem Soc       Date:  2021-11-30       Impact factor: 15.419

2.  Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles.

Authors:  Marco A Lopez; Joshua A Buss; Shannon S Stahl
Journal:  Org Lett       Date:  2021-12-29       Impact factor: 6.005

3.  Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides.

Authors:  Sii Hong Lau; Meredith A Borden; Talia J Steiman; Lucy S Wang; Marvin Parasram; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2021-09-20       Impact factor: 15.419

Review 4.  Stereoinduction in Metallaphotoredox Catalysis.

Authors:  Alexander Lipp; Shorouk O Badir; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-01       Impact factor: 15.336

5.  Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

Authors:  Jianyu Xu; Olivia P Bercher; Michael R Talley; Mary P Watson
Journal:  ACS Catal       Date:  2021-01-19       Impact factor: 13.084

6.  Synthesis of Axially Chiral 2,2'-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution.

Authors:  Ziqing Zuo; Raphael S Kim; Donald A Watson
Journal:  J Am Chem Soc       Date:  2021-01-13       Impact factor: 15.419

7.  Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

Authors:  Beatrice Lansbergen; Paola Granatino; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-05-24       Impact factor: 15.419

8.  General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.

Authors:  Lei Guo; Mingbin Yuan; Yanyan Zhang; Fang Wang; Shengqing Zhu; Osvaldo Gutierrez; Lingling Chu
Journal:  J Am Chem Soc       Date:  2020-11-19       Impact factor: 15.419

9.  Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides.

Authors:  Travis J DeLano; Sara E Dibrell; Caitlin R Lacker; Adam R Pancoast; Kelsey E Poremba; Leah Cleary; Matthew S Sigman; Sarah E Reisman
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

10.  Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

Authors:  Zhiyang Lin; Youxiang Jin; Weitao Hu; Chuan Wang
Journal:  Chem Sci       Date:  2021-04-09       Impact factor: 9.825

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