Literature DB >> 30307672

Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights.

Jennifer K Matsui1, Álvaro Gutiérrez-Bonet1, Madeline Rotella2, Rauful Alam1, Osvaldo Gutierrez2, Gary A Molander1.   

Abstract

A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and α-alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DFT and DLPNO-CCSD(T)] support the mechanistic hypothesis of a Ni0 to NiII oxidative addition pathway followed by radical addition and inner-sphere allylation.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic compounds; nickel; photochemistry; reaction mechanisms; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 30307672      PMCID： PMC6526374          DOI： 10.1002/anie.201809919

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


  35 in total

1.  Tsuji-trost allylic alkylation with ketone enolates.

Authors:  Manfred Braun; Thorsten Meier
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-27       Impact factor: 15.336

2.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.

Authors:  Barry M Trost; Michelle R Machacek; Aaron Aponick
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

3.  Iridium-catalyzed regio- and enantioselective allylation of ketone enolates.

Authors:  Timm Graening; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

4.  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

5.  Raising the pKa limit of "soft" nucleophiles in palladium-catalyzed allylic substitutions: application of diarylmethane pronucleophiles.

Authors:  Sheng-Chun Sha; Jiadi Zhang; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2013-11-12       Impact factor: 15.419

Review 6.  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

7.  1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis.

Authors:  Álvaro Gutiérrez-Bonet; John C Tellis; Jennifer K Matsui; Brandon A Vara; Gary A Molander
Journal:  ACS Catal       Date:  2016-10-27       Impact factor: 13.084

8.  Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis.

Authors:  Javad Amani; Gary A Molander
Journal:  J Org Chem       Date:  2017-01-17       Impact factor: 4.354

9.  Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis.

Authors:  Niki R Patel; Christopher B Kelly; Matthieu Jouffroy; Gary A Molander
Journal:  Org Lett       Date:  2016-02-01       Impact factor: 6.005

10.  Structural characterisation of the capsular polysaccharide expressed by Burkholderia thailandensis strain E555:: wbiI (pKnock-KmR) and assessment of the significance of the 2-O-acetyl group in immune protection.

Authors:  Marc Bayliss; Matthew I Donaldson; Sergey A Nepogodiev; Giulia Pergolizzi; Andrew E Scott; Nicholas J Harmer; Robert A Field; Joann L Prior
Journal:  Carbohydr Res       Date:  2017-09-21       Impact factor: 2.975
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  9 in total

1.  Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis.

Authors:  Youran Luo; Álvaro Gutiérrez-Bonet; Jennifer K Matsui; Madeline E Rotella; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  ACS Catal       Date:  2019-08-28       Impact factor: 13.084

2.  Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach.

Authors:  Zheng-Jun Wang; Shuai Zheng; Eugénie Romero; Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2019-08-07       Impact factor: 6.005

3.  Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox-Catalyzed C(sp2)-C(sp3) Cross-Couplings.

Authors:  Mingbin Yuan; Osvaldo Gutierrez
Journal:  Wiley Interdiscip Rev Comput Mol Sci       Date:  2021-09-21

4.  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

5.  Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.

Authors:  Mark W Campbell; Mingbin Yuan; Viktor C Polites; Osvaldo Gutierrez; Gary A Molander
Journal:  J Am Chem Soc       Date:  2021-03-04       Impact factor: 15.419

6.  2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.

Authors:  Oliver Fischer; Markus R Heinrich
Journal:  Chemistry       Date:  2021-02-24       Impact factor: 5.236

7.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

8.  Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism.

Authors:  Huifeng Yue; Chen Zhu; Rajesh Kancherla; Fangying Liu; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336

9.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622
  9 in total

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