Literature DB >> 32996312

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling.

Jacob R Ludwig1, Eric M Simmons2, Steven R Wisniewski2, Paul J Chirik1.   

Abstract

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

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Year:  2020        PMID： 32996312      PMCID： PMC7867578          DOI： 10.1021/acs.orglett.0c02934

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


  35 in total

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4.  Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Unactivated Arylboronic Esters.

Authors:  Michael P Crockett; Chet C Tyrol; Alexander S Wong; Bo Li; Jeffery A Byers
Journal:  Org Lett       Date:  2018-08-22       Impact factor: 6.005

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Authors:  Fu-She Han
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8.  An Improved System for the Aqueous Lipshutz-Negishi Cross-Coupling of Alkyl Halides with Aryl Electrophiles.

Authors:  Vasudev R Bhonde; Brian T O'Neill; Stephen L Buchwald
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Review 9.  Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes.

Authors:  Gregory C Fu
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Review 10.  Recent developments in the Suzuki-Miyaura reaction: 2010-2014.

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  2 in total

1.  Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands.

Authors:  L Reginald Mills; David Gygi; Jacob R Ludwig; Eric M Simmons; Steven R Wisniewski; Junho Kim; Paul J Chirik
Journal:  ACS Catal       Date:  2022-01-20       Impact factor: 13.700

2.  Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons.

Authors:  Zhenhua Zhang; Bartosz Górski; Daniele Leonori
Journal:  J Am Chem Soc       Date:  2022-01-21       Impact factor: 16.383
  2 in total

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