Literature DB >> 33041649

Recent Advances in Radical Addition to Alkenylboron Compounds.

Gabriel J Lovinger1, James P Morken1.   

Abstract

The addition of carbon-centered radicals to alkenylboron compounds provides a useful method for the construction of organoboron reagents which are versatile reagents in chemical synthesis. While the first examples of this type or process appeared 70 years ago, until recently, attention to this type of reaction has been limited. A number of examples of this reactivity have been demonstrated recently, and strategies are emerging that allow for tuning the reagent structure in order to modulate reactivity. This review surveys recent advances in this class of reaction.

Entities:  

Keywords:  Addition Reactions; Carbon Radicals; Catalysis; Organoboron; Stereocontrol

Year:  2019        PMID: 33041649      PMCID: PMC7546537          DOI: 10.1002/ejoc.201901600

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  23 in total

Review 1.  Catalysis of Radical Reactions: A Radical Chemistry Perspective.

Authors:  Armido Studer; Dennis P Curran
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-13       Impact factor: 15.336

2.  Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes.

Authors:  Mattia Silvi; Christopher Sandford; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-04-17       Impact factor: 15.419

3.  Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates.

Authors:  Béatrice Quiclet-Sire; Samir Z Zard
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

4.  Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters.

Authors:  Mattia Silvi; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2019-06-05       Impact factor: 15.419

5.  Radical-Triggered Three-Component Coupling Reaction of Alkenylboronates, α-Halocarbonyl Compounds, and Organolithium Reagents: The Inverse Ylid Mechanism.

Authors:  Nicholas D C Tappin; Manuel Gnägi-Lux; Philippe Renaud
Journal:  Chemistry       Date:  2018-07-13       Impact factor: 5.236

6.  Nickel-Catalyzed Umpolung Arylation of Ambiphilic α-Bromoalkyl Boronic Esters.

Authors:  Shang-Zheng Sun; Ruben Martin
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-01       Impact factor: 15.336

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

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

8.  The First Boron-Tethered Radical Cyclizations and Intramolecular Homolytic Substitutions at Boron.

Authors:  Robert A Batey; David V Smil
Journal:  Angew Chem Int Ed Engl       Date:  1999-06-14       Impact factor: 15.336

9.  Functionalized olefin cross-coupling to construct carbon-carbon bonds.

Authors:  Julian C Lo; Jinghan Gui; Yuki Yabe; Chung-Mao Pan; Phil S Baran
Journal:  Nature       Date:  2014-12-18       Impact factor: 49.962

10.  Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade.

Authors:  Chao Shu; Riccardo S Mega; Björn J Andreassen; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-25       Impact factor: 15.336

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  6 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.  Generation of α-Boryl Radicals by H. Transfer and their Use in Cycloisomerizations.

Authors:  Shicheng Shi; Farbod Salahi; Hunter B Vibbert; Maleeha Rahman; Scott A Snyder; Jack R Norton
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

3.  Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Authors:  Mingkai Zhang; Peilin Xu; Alex J Vendola; Christophe Allais; Anne-Marie Dechert Schmitt; Robert A Singer; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-08       Impact factor: 16.823

4.  Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Authors:  Colton R Davis; Irungu K Luvaga; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2021-03-23       Impact factor: 15.419

5.  Visible light-driven Giese reaction with alkyl tosylates catalysed by nucleophilic cobalt.

Authors:  Kimihiro Komeyama; Takuya Michiyuki; Yoshikazu Teshima; Itaru Osaka
Journal:  RSC Adv       Date:  2021-01-18       Impact factor: 3.361

Review 6.  The Impact of Boron Hybridisation on Photocatalytic Processes.

Authors:  Alessandro Marotta; Callum E Adams; John J Molloy
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-10       Impact factor: 16.823

  6 in total

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