Literature DB >> 27380912

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

Jie Wang1, Tian Qin1, Tie-Gen Chen1, Laurin Wimmer1, Jacob T Edwards1, Josep Cornella1, Benjamin Vokits2, Scott A Shaw2, Phil S Baran3.   

Abstract

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2 ⋅6 H2 O-$9.5 mol(-1) , Et3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Suzuki cross-coupling; decarboxylation; homogeneous catalysis; nickel catalysts; redox-active esters

Mesh：

Substances：

Year:  2016        PMID： 27380912      PMCID： PMC5232357          DOI： 10.1002/anie.201605463

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  25 in total

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Authors:  Dean G Brown; Jonas Boström
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2.  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

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Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
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4.  Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Authors:  Soumik Biswas; Daniel J Weix
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5.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

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.  Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions.

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Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

8.  Ni-catalyzed cascade formation of C(sp3)--C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides.

Authors:  Vilas B Phapale; Elena Buñuel; Miguel García-Iglesias; Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation.

Authors:  Nathan D Schley; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

10.  Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides.

Authors:  Kierra M M Huihui; Jill A Caputo; Zulema Melchor; Astrid M Olivares; Amanda M Spiewak; Keywan A Johnson; Tarah A DiBenedetto; Seoyoung Kim; Laura K G Ackerman; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2016-04-11       Impact factor: 15.419
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  37 in total

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Authors:  Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

2.  Decarboxylative borylation.

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

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4.  A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

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Journal:  Angew Chem Int Ed Engl       Date:  2018-10-15       Impact factor: 15.336

5.  Suzuki-Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon-Carbon Bonds.

Authors:  Ying Xia; Jianchun Wang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-04-17       Impact factor: 15.419

6.  Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.

Authors:  Kirk W Shimkin; John Montgomery
Journal:  J Am Chem Soc       Date:  2018-05-31       Impact factor: 15.419

7.  Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Authors:  Cian Kingston; Michael A Wallace; Alban J Allentoff; Justine N deGruyter; Jason S Chen; Sharon X Gong; Samuel Bonacorsi; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-01-03       Impact factor: 15.419

8.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
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9.  Radical Retrosynthesis.

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Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

10.  CITU: A Peptide and Decarboxylative Coupling Reagent.

Authors:  Justine N deGruyter; Lara R Malins; Laurin Wimmer; Khalyd J Clay; Javier Lopez-Ogalla; Tian Qin; Josep Cornella; Zhiqing Liu; Guanda Che; Denghui Bao; Jason M Stevens; Jennifer X Qiao; Martin P Allen; Michael A Poss; Phil S Baran
Journal:  Org Lett       Date:  2017-11-08       Impact factor: 6.005
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