Literature DB >> 30917282

Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Jennie Liao1, Corey H Basch1, Megan E Hoerrner1, Michael R Talley1, Brian P Boscoe2, Joseph W Tucker2, Michelle R Garnsey2, Mary P Watson1.   

Abstract

A nickel-catalyzed reductive cross-coupling of <span class="Chemical">alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.

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Year:  2019        PMID： 30917282      PMCID： PMC6517243          DOI： 10.1021/acs.orglett.9b01014

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  55 in total

1.  Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents.

Authors:  Manuel Guisán-Ceinos; Victor Martín-Heras; Mariola Tortosa
Journal:  J Am Chem Soc       Date:  2017-06-15       Impact factor: 15.419

2.  Engaging nonaromatic, heterocyclic tosylates in reductive cross-coupling with aryl and heteroaryl bromides.

Authors:  Gary A Molander; Kaitlin M Traister; Brian T O'Neill
Journal:  J Org Chem       Date:  2015-02-25       Impact factor: 4.354

3.  Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2.

Authors:  Toni Moragas; Morgane Gaydou; Ruben Martin
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-16       Impact factor: 15.336

4.  Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage.

Authors:  Jiefeng Hu; Heqing Sun; Wangshui Cai; Xinghui Pu; Yemin Zhang; Zhuangzhi Shi
Journal:  J Org Chem       Date:  2015-12-15       Impact factor: 4.354

5.  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

6.  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

7.  Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.

Authors:  Corey H Basch; Kelsey M Cobb; Mary P Watson
Journal:  Org Lett       Date:  2015-12-17       Impact factor: 6.005

8.  Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides.

Authors:  Xuan Wang; Guobin Ma; Yu Peng; Chloe E Pitsch; Brenda J Moll; Thu D Ly; Xiaotai Wang; Hegui Gong
Journal:  J Am Chem Soc       Date:  2018-10-22       Impact factor: 15.419

9.  Photoinduced Deaminative Borylation of Alkylamines.

Authors:  Jingjing Wu; Lin He; Adam Noble; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2018-08-21       Impact factor: 15.419

10.  1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis.

Authors:  Álvaro Gutiérrez-Bonet; John C Tellis; Jennifer K Matsui; Brandon A Vara; Gary A Molander
Journal:  ACS Catal       Date:  2016-10-27       Impact factor: 13.084
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  15 in total

1.  Deaminative Arylation of Amino Acid-derived Pyridinium Salts.

Authors:  Megan E Hoerrner; Kristen M Baker; Corey H Basch; Earl M Bampo; Mary P Watson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

Review 2.  Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

Authors:  Yuan Gao; Songwei Jiang; Nian-Dong Mao; Huan Xiang; Ji-Long Duan; Xiang-Yang Ye; Li-Wei Wang; Yang Ye; Tian Xie
Journal:  Top Curr Chem (Cham)       Date:  2022-05-19

3.  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

4.  In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides.

Authors:  Benjamin K Chi; Jonas K Widness; Michael M Gilbert; Daniel C Salgueiro; Kevin J Garcia; Daniel J Weix
Journal:  ACS Catal       Date:  2021-12-21       Impact factor: 13.084

5.  Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.

Authors:  Julia R Dorsheimer; Melissa A Ashley; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-12       Impact factor: 15.419

6.  Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

Authors:  Bill J Motsch; Sarah E Wengryniuk
Journal:  Org Lett       Date:  2022-08-08       Impact factor: 6.072

7.  Deaminative Reductive Methylation of Alkylpyridinium Salts.

Authors:  Olivia P Bercher; Shane Plunkett; Thomas E Mortimer; Mary P Watson
Journal:  Org Lett       Date:  2021-08-31       Impact factor: 6.072

8.  α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.

Authors:  Kristen M Baker; Amanda Tallon; Richard P Loach; Olivia P Bercher; Matthew A Perry; Mary P Watson
Journal:  Org Lett       Date:  2021-09-27       Impact factor: 6.072

9.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

10.  Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines.

Authors:  Jianyu Xu; J Cameron Twitty; Mary P Watson
Journal:  Org Lett       Date:  2021-07-30       Impact factor: 6.072
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