Literature DB >> 31953874

Identification of the Active Catalyst for Nickel-Catalyzed Stereospecific Kumada Coupling Reactions of Ethers.

David D Dawson1, Victoria F Oswald1, Andy S Borovik1, Elizabeth R Jarvo1.   

Abstract

A series of nickel complexes in varying oxidation states were evaluated as precatalysts for the stereospecific cross-coupling of benzylic ethers. These results demonstrate rapid redox reactions of precatalysts, such that the oxidative state of the precatalyst does not dictate the oxidation state of the active catalyst in solution. These data provide the first experimental evidence for a Ni0 -NiII catalytic cycle for a stereospecific alkyl-alkyl cross-coupling reaction, including spectroscopic analysis of the catalyst resting state.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  absorption spectroscopy; cross-coupling mechanism; nickel catalysis; organic chemistry; precatalyst

Year:  2020        PMID： 31953874      PMCID： PMC7872209          DOI： 10.1002/chem.202000215

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  27 in total

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2.  Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings.

Authors:  Susan L Zultanski; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-09-13       Impact factor: 15.419

3.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

4.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: enantioselective synthesis of diarylethanes.

Authors:  Buck L H Taylor; Elizabeth C Swift; Joshua D Waetzig; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2010-12-14       Impact factor: 15.419

5.  Nickel-catalyzed Negishi alkylations of styrenyl aziridines.

Authors:  Chung-Yang Huang; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-03-16       Impact factor: 15.419

6.  Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I).

Authors:  Louise M Guard; Megan Mohadjer Beromi; Gary W Brudvig; Nilay Hazari; David J Vinyard
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-11       Impact factor: 15.336

Review 7.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

8.  Controlling first-row catalysts: amination of aryl and heteroaryl chlorides and bromides with primary aliphatic amines catalyzed by a BINAP-ligated single-component Ni(0) complex.

Authors:  Shaozhong Ge; Rebecca A Green; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-01-21       Impact factor: 15.419

9.  A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes.

Authors:  Eric A Standley; Stacey J Smith; Peter Müller; Timothy F Jamison
Journal:  Organometallics       Date:  2014-04-16       Impact factor: 3.876

10.  Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers with Isotopically-Labeled Grignard Reagents.

Authors:  David D Dawson; Elizabeth R Jarvo
Journal:  Org Process Res Dev       Date:  2015-09-11       Impact factor: 3.317
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  2 in total

1.  Effects of the halogenido ligands on the Kumada-coupling catalytic activity of [Ni{ t BuN(PPh2)2-κ2P}X2], X = Cl, Br, I, complexes.

Authors:  Polydoros-Chrysovalantis Ioannou; Radek Coufal; Kalliopi Kakridi; Catherine P Raptopoulou; Olga Trhlíková; Vassilis Psycharis; Jiří Zedník; Panayotis Kyritsis; Jiří Vohlídal
Journal:  RSC Adv       Date:  2022-01-14       Impact factor: 3.361

2.  Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Authors:  Amberly B Sanford; Elizabeth R Jarvo
Journal:  Synlett       Date:  2020-11-27       Impact factor: 2.454
  2 in total

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