Literature DB >> 18052180

Ni-catalyzed mild arylation of alpha-halocarbonyl compounds with arylboronic acids.

Chao Liu1, Chuan He, Wei Shi, Mao Chen, Aiwen Lei.   

Abstract

A simple yet powerful Ni catalyst can be used to promote direct arylations of alpha-halocarbonyl compounds, including a range of esters, amides, and ketones, with various arylboronic acids under mild conditions. The method tolerates beta-hydrogens and functional groups in the substrates and offers reactivity and selectivity profiles that are complementary to those found in the well-established Buchwald-Hartwig approach.

Entities:  

Year:  2007        PMID: 18052180     DOI: 10.1021/ol702456z

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


  8 in total

Review 1.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

2.  A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides.

Authors:  Tiffany Q Chen; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-05       Impact factor: 15.336

3.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

4.  Catalytic asymmetric cross-couplings of racemic alpha-bromoketones with arylzinc reagents.

Authors:  Pamela M Lundin; Jorge Esquivias; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Palladium-catalyzed α-arylation of zinc enolates of esters: reaction conditions and substrate scope.

Authors:  Takuo Hama; Shaozhong Ge; John F Hartwig
Journal:  J Org Chem       Date:  2013-08-21       Impact factor: 4.354

6.  Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

Authors:  Gary A Molander; Kaitlin M Traister; Thiago Barcellos
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

7.  C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling.

Authors:  Aristidis Vasilopoulos; Shane W Krska; Shannon S Stahl
Journal:  Science       Date:  2021-04-23       Impact factor: 47.728

8.  Iridium-catalyzed 1,3-hydrogen shift/chlorination of allylic alcohols.

Authors:  Nanna Ahlsten; Antonio Bermejo Gómez; Belén Martín-Matute
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

  8 in total

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