Literature DB >> 21090594

Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides.

Gary A Molander1, O Andreea Argintaru, Ioana Aron, Spencer D Dreher.   

Abstract

A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved.

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Year:  2010        PMID： 21090594      PMCID： PMC3075421          DOI： 10.1021/ol102717x

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


  18 in total

1.  Amino alcohols as ligands for nickel-catalyzed suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids.

Authors:  Francisco González-Bobes; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

2.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

Review 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Negishi alkyl-aryl cross-coupling catalyzed by Rh: efficiency of novel tripodal 3-diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl acetate ligand.

Authors:  Syogo Ejiri; Shunsuke Odo; Hideki Takahashi; Yugo Nishimura; Kazuma Gotoh; Yasushi Nishihara; Kentaro Takagi
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

5.  Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors:  Nathan A Owston; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

6.  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

7.  Stereospecific Suzuki cross-coupling of alkyl alpha-cyanohydrin triflates.

Authors:  Anyu He; J R Falck
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

8.  A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.

Authors:  David M Knapp; Eric P Gillis; Martin D Burke
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

9.  Preparation of aryloxetanes and arylazetidines by use of an alkyl-aryl suzuki coupling.

Authors:  Matthew A J Duncton; M Angels Estiarte; Darlene Tan; Carl Kaub; Donogh J R O'Mahony; Russell J Johnson; Matthew Cox; William T Edwards; Min Wan; John Kincaid; Michael G Kelly
Journal:  Org Lett       Date:  2008-07-09       Impact factor: 6.005

10.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354
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  7 in total

1.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

2.  Metal-free chlorodeboronation of organotrifluoroborates.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2011-08-03       Impact factor: 4.354

3.  Alkyl-(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis.

Authors:  Frederik Sandfort; Matthew J O'Neill; Josep Cornella; Laurin Wimmer; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-10       Impact factor: 15.336

4.  Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors:  Michael T Bovino; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-05       Impact factor: 15.336

5.  Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.

Authors:  Daniel A Everson; Brittany A Jones; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

6.  Practical and Regioselective Synthesis of C-4-Alkylated Pyridines.

Authors:  Jin Choi; Gabriele Laudadio; Edouard Godineau; Phil S Baran
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 16.383

7.  Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.

Authors:  Gary A Molander; O Andreea Argintaru
Journal:  Org Lett       Date:  2014-03-25       Impact factor: 6.005
  7 in total

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