Literature DB >> 21553878

Nickel-catalyzed Kumada cross-coupling reactions of tertiary alkylmagnesium halides and aryl bromides/triflates.

Amruta Joshi-Pangu1, Chao-Yuan Wang, Mark R Biscoe.   

Abstract

We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of n class="Chemical">aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.

Entities:  

Year:  2011        PMID： 21553878      PMCID： PMC8036247          DOI： 10.1021/ja202769t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  25 in total

1.  The measure of all rings--N-heterocyclic carbenes.

Authors:  Thomas Dröge; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-17       Impact factor: 15.336

Review 2.  Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions.

Authors:  Alena Rudolph; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature.

Authors:  Sean W Smith; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

5.  Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation.

Authors:  Spencer D Dreher; Peter G Dormer; Deidre L Sandrock; Gary A Molander
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

6.  Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions.

Authors:  Brett P Fors; Philipp Krattiger; Eric Strieter; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-07-12       Impact factor: 6.005

7.  An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: serendipity rules.

Authors:  William A Nugent
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

8.  Evidence for a NiI active species in the catalytic cross-coupling of alkyl electrophiles.

Authors:  Thomas J Anderson; Gavin D Jones; David A Vicic
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

9.  Direct aminoalkylation of arenes and hetarenes via Ni-catalyzed Negishi cross-coupling reactions.

Authors:  Laurin Melzig; Andrey Gavryushin; Paul Knochel
Journal:  Org Lett       Date:  2007-11-30       Impact factor: 6.005

10.  Surveying sterically demanding N-heterocyclic carbene ligands with restricted flexibility for palladium-catalyzed cross-coupling reactions.

Authors:  Sebastian Würtz; Frank Glorius
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384
View more
  27 in total

1.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

2.  Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer.

Authors:  David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-07-18       Impact factor: 15.419

3.  Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Authors:  Tie-Gen Chen; Haolin Zhang; Pavel K Mykhailiuk; Rohan R Merchant; Courtney A Smith; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-30       Impact factor: 15.336

4.  Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis.

Authors:  Gregory L Lackner; Kyle W Quasdorf; Gerald Pratsch; Larry E Overman
Journal:  J Org Chem       Date:  2015-06-01       Impact factor: 4.354

5.  Stereospecific Palladium-Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.

Authors:  Chao-Yuan Wang; Glenn Ralph; Joseph Derosa; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

6.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

7.  Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors:  Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-09       Impact factor: 15.336

8.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

9.  Nickel-catalyzed carbon-carbon bond-forming reactions of unactivated tertiary alkyl halides: Suzuki arylations.

Authors:  Susan L Zultanski; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2013-01-02       Impact factor: 15.419

10.  On the Nature of C(sp3)-C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides.

Authors:  Mingbin Yuan; Zhihui Song; Shorouk O Badir; Gary A Molander; Osvaldo Gutierrez
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.