Literature DB >> 26014029

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Lingling Chu1, Jeffrey M Lipshultz1, David W C MacMillan2.   

Abstract

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arylation; decarboxylation; nickel catalysis; photoredox catalysis; α-oxo acids

Mesh:

Substances:

Year:  2015        PMID: 26014029      PMCID: PMC4526169          DOI: 10.1002/anie.201501908

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


  26 in total

1.  Visible light photoredox catalysis: applications in organic synthesis.

Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

Review 2.  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

3.  Direct C-F bond formation using photoredox catalysis.

Authors:  Montserrat Rueda-Becerril; Olivier Mahé; Myriam Drouin; Marek B Majewski; Julian G West; Michael O Wolf; Glenn M Sammis; Jean-François Paquin
Journal:  J Am Chem Soc       Date:  2014-01-30       Impact factor: 15.419

4.  Hydroacylation of alpha,beta-unsaturated esters via aerobic C-H activation.

Authors:  Vijay Chudasama; Richard J Fitzmaurice; Stephen Caddick
Journal:  Nat Chem       Date:  2010-06-06       Impact factor: 24.427

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

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

7.  Visible-light-mediated decarboxylation/oxidative amidation of α-keto acids with amines under mild reaction conditions using O(2).

Authors:  Jie Liu; Qiang Liu; Hong Yi; Chu Qin; Ruopeng Bai; Xiaotian Qi; Yu Lan; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-24       Impact factor: 15.336

8.  Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides.

Authors:  Adam Noble; Stefan J McCarver; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

9.  Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore.

Authors:  Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419

10.  Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors:  Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-07-28       Impact factor: 15.419

View more
  36 in total

1.  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

2.  Alkyl-(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis.

Authors:  Frederik Sandfort; Matthew J O'Neill; Josep Cornella; Laurin Wimmer; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-10       Impact factor: 15.336

3.  A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist.

Authors:  James J Douglas; Haley Albright; Martin J Sevrin; Kevin P Cole; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-16       Impact factor: 15.336

4.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

5.  Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

6.  Ketone Synthesis from Benzyldiboronates and Esters: Leveraging α-Boryl Carbanions for Carbon-Carbon Bond Formation.

Authors:  Boran Lee; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2020-01-24       Impact factor: 15.419

7.  Accessing Elaborated 2,1-Borazaronaphthalene Cores Using Photoredox/Nickel Dual-Catalytic Functionalization.

Authors:  Matthieu Jouffroy; Geraint H M Davies; Gary A Molander
Journal:  Org Lett       Date:  2016-03-17       Impact factor: 6.005

8.  Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis.

Authors:  Candice L Joe; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

9.  Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Authors:  Arghya Banerjee; Zhen Lei; Ming-Yu Ngai
Journal:  Synthesis (Stuttg)       Date:  2018-12-12       Impact factor: 3.157

10.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.