Literature DB >> 25650892

Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

David N Primer1, Idris Karakaya, John C Tellis, Gary A Molander.   

Abstract

Single-electron-mediated alkyl transfer affords a novel mechanism for transmetalation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyltrifluoroborates with an array of aryl bromides mediated by an Ir photoredox catalyst and a Ni cross-coupling catalyst.

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Year:  2015        PMID： 25650892      PMCID： PMC4466116          DOI： 10.1021/ja512946e

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


  31 in total

1.  Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.

Authors:  Amadeu Bonet; Marcin Odachowski; Daniele Leonori; Stephanie Essafi; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-06-08       Impact factor: 24.427

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

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

Authors:  Jan Breitenfeld; Jesus Ruiz; Matthew D Wodrich; Xile Hu
Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

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.  Base-promoted protodeboronation of 2,6-disubstituted arylboronic acids.

Authors:  Jerome Lozada; Zhibo Liu; David M Perrin
Journal:  J Org Chem       Date:  2014-05-20       Impact factor: 4.354

9.  Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides.

Authors:  Ling Li; Chao-Yuan Wang; Rongcai Huang; Mark R Biscoe
Journal:  Nat Chem       Date:  2013-05-19       Impact factor: 24.427

10.  Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors:  Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal:  J Am Chem Soc       Date:  2014-09-23       Impact factor: 15.419
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  72 in total

1.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors:  Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

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.  Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

Authors:  Christopher B Kelly; Niki R Patel; David N Primer; Matthieu Jouffroy; John C Tellis; Gary A Molander
Journal:  Nat Protoc       Date:  2017-02-02       Impact factor: 13.491

4.  1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

Authors:  Daniel Kaiser; Adam Noble; Valerio Fasano; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

5.  Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Authors:  Rauful Alam; Gary A Molander
Journal:  J Org Chem       Date:  2017-11-27       Impact factor: 4.354

6.  Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors:  Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-12-22       Impact factor: 15.419

7.  Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Authors:  Jun Yi; Shorouk O Badir; Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2019-05-30       Impact factor: 6.005

8.  Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates.

Authors:  Shuai Zheng; David N Primer; Gary A Molander
Journal:  ACS Catal       Date:  2017-10-25       Impact factor: 13.084

9.  α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Authors:  Mirna El Khatib; Ricardo Augusto Massarico Serafim; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

10.  The Cleavage of a C-C Bond in Cyclobutylanilines by Visible-Light Photoredox Catalysis: Development of a [4+2] Annulation Method.

Authors:  Jiang Wang; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-24       Impact factor: 15.336
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