Literature DB >> 28471521

Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals.

Matthew K Nielsen1, Benjamin J Shields1, Junyi Liu1, Michael J Williams2, Michael J Zacuto2, Abigail G Doyle1.   

Abstract

We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; formylation; nickel; photocatalysis; redox reactions

Mesh：

Substances：

Year:  2017        PMID： 28471521      PMCID： PMC5662441          DOI： 10.1002/anie.201702079

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


  11 in total

1.  A general and efficient method for the formylation of aryl and heteroaryl bromides.

Authors:  Stefan Klaus; Helfried Neumann; Alexander Zapf; Dirk Strübing; Sandra Hübner; Juan Almena; Thomas Riermeier; Peter Gross; Martin Sarich; Wolf-Rüdiger Krahnert; Kai Rossen; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-16       Impact factor: 15.336

2.  Palladium-catalyzed formylation of aryl halides with tert-butyl isocyanide.

Authors:  Xiao Jiang; Jin-Mei Wang; Ying Zhang; Zhong Chen; Yong-Ming Zhu; Shun-Jun Ji
Journal:  Org Lett       Date:  2014-06-23       Impact factor: 6.005

3.  Pd/C-catalyzed direct formylation of aromatic iodides to aryl aldehydes using carbon dioxide as a C1 resource.

Authors:  Bo Yu; Yanfei Zhao; Hongye Zhang; Jilei Xu; Leiduan Hao; Xiang Gao; Zhimin Liu
Journal:  Chem Commun (Camb)       Date:  2014-01-21       Impact factor: 6.222

4.  Palladium-catalyzed reductive carbonylation of aryl halides with N-formylsaccharin as a CO source.

Authors:  Tsuyoshi Ueda; Hideyuki Konishi; Kei Manabe
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-03       Impact factor: 15.336

5.  Concise syntheses of (-)-galanthamine and (+/-)-codeine via intramolecular alkylation of a phenol derivative.

Authors:  Philip Magnus; Neeraj Sane; Benjamin P Fauber; Vince Lynch
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

6.  Introducing genetically encoded aldehydes into proteins.

Authors:  Isaac S Carrico; Brian L Carlson; Carolyn R Bertozzi
Journal:  Nat Chem Biol       Date:  2007-04-22       Impact factor: 15.040

7.  Direct C(sp3)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals.

Authors:  Benjamin J Shields; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2016-09-21       Impact factor: 15.419

8.  Native functionality in triple catalytic cross-coupling: sp³ C-H bonds as latent nucleophiles.

Authors:  Megan H Shaw; Valerie W Shurtleff; Jack A Terrett; James D Cuthbertson; David W C MacMillan
Journal:  Science       Date:  2016-04-28       Impact factor: 47.728

9.  Palladium-catalyzed carbonylations of aryl bromides using paraformaldehyde: synthesis of aldehydes and esters.

Authors:  Kishore Natte; Andreas Dumrath; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-28       Impact factor: 15.336

10.  Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations.

Authors:  Drew R Heitz; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2016-09-21       Impact factor: 15.419
View more
  13 in total

1.  Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Authors:  Yifan Deng; Minh D Nguyen; Yike Zou; K N Houk; Amos B Smith
Journal:  Org Lett       Date:  2019-02-26       Impact factor: 6.005

2.  Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.

Authors:  Stavros K Kariofillis; Benjamin J Shields; Makeda A Tekle-Smith; Michael J Zacuto; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-10       Impact factor: 15.419

3.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

4.  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

5.  Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C-O Bonds in Cyclic Acetals.

Authors:  Ciro Romano; Laura Talavera; Enrique Gómez-Bengoa; Ruben Martin
Journal:  J Am Chem Soc       Date:  2022-06-24       Impact factor: 16.383

6.  Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Authors:  Vladimir Maslivetc; Colby Barrett; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2018-01-03       Impact factor: 3.876

Review 7.  Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

Authors:  John A Milligan; James P Phelan; Shorouk O Badir; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

8.  Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)-H Cross-Coupling.

Authors:  Stavros K Kariofillis; Abigail G Doyle
Journal:  Acc Chem Res       Date:  2021-01-29       Impact factor: 22.384

Review 9.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

10.  Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis.

Authors:  Leitao Huan; Xiaomin Shu; Weisai Zu; Haohua Huo
Journal:  Nat Commun       Date:  2021-06-10       Impact factor: 14.919
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.