Literature DB >> 25209429

Radical C-H functionalization of heteroarenes under electrochemical control.

Alexander G O'Brien1, Akinobu Maruyama, Yasuhide Inokuma, Makoto Fujita, Phil S Baran, Donna G Blackmond.   

Abstract

Electrochemical reactions are shown to be effective for the C-H functionalization of a number of heterocyclic substrates that are recalcitrant to conventional peroxide radical initiation conditions. Monitoring reaction progress under electrochemical conditions provides mechanistic insight into the C-H functionalization of a series of heterocycles of interest in medicinal chemistry.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; electrochemistry; heterocycles; radical reactions; reaction mechanisms

Mesh:

Substances:

Year:  2014        PMID: 25209429      PMCID: PMC4214156          DOI: 10.1002/anie.201407948

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


  16 in total

1.  Chemical Redox Agents for Organometallic Chemistry.

Authors:  Neil G. Connelly; William E. Geiger
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

2.  Novel triarylimidazole redox catalysts: synthesis, electrochemical properties, and applicability to electrooxidative C-H activation.

Authors:  Cheng-chu Zeng; Ni-tao Zhang; Chiu Marco Lam; R Daniel Little
Journal:  Org Lett       Date:  2012-02-16       Impact factor: 6.005

3.  Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol.

Authors:  Axel Kirste; Bernd Elsler; Gregor Schnakenburg; Siegfried R Waldvogel
Journal:  J Am Chem Soc       Date:  2012-02-13       Impact factor: 15.419

4.  Bioconjugation by native chemical tagging of C-H bonds.

Authors:  Qianghui Zhou; Jinghan Gui; Chung-Mao Pan; Earl Albone; Xin Cheng; Edward M Suh; Luigi Grasso; Yoshihiro Ishihara; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-08-22       Impact factor: 15.419

5.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

6.  Electron transfer properties of alkoxyl radicals. A time-resolved kinetic study of the reactions of the tert-butoxyl, cumyloxyl, and benzyloxyl radicals with alkyl ferrocenes.

Authors:  Massimo Bietti; Gino A DiLabio; Osvaldo Lanzalunga; Michela Salamone
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

7.  Innate C-H trifluoromethylation of heterocycles.

Authors:  Yining Ji; Tobias Brueckl; Ryan D Baxter; Yuta Fujiwara; Ian B Seiple; Shun Su; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2011-08-15       Impact factor: 11.205

8.  A new reagent for direct difluoromethylation.

Authors:  Yuta Fujiwara; Janice A Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Darryl D Dixon; Michael R Collins; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2012-01-13       Impact factor: 15.419

9.  Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies.

Authors:  E Paige Stout; Michael Y Choi; Januario E Castro; Tadeusz F Molinski
Journal:  J Med Chem       Date:  2014-06-10       Impact factor: 7.446

10.  Practical and innate carbon-hydrogen functionalization of heterocycles.

Authors:  Yuta Fujiwara; Janice A Dixon; Fionn O'Hara; Erik Daa Funder; Darryl D Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Bart Herlé; Neal Sach; Michael R Collins; Yoshihiro Ishihara; Phil S Baran
Journal:  Nature       Date:  2012-11-28       Impact factor: 49.962

View more
  23 in total

1.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

2.  Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Authors:  Zhichao Lu; Olivia Hennis; Joseph Gentry; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2020-05-13       Impact factor: 6.005

3.  Improvements to the Practical Usability of the "Crystalline Sponge" Method for Organic Structure Determination.

Authors:  Greyson W Waldhart; Neal P Mankad; Bernard D Santarsiero
Journal:  Org Lett       Date:  2016-11-15       Impact factor: 6.005

4.  Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.

Authors:  Yu Kawamata; Julien C Vantourout; David P Hickey; Peng Bai; Longrui Chen; Qinglong Hou; Wenhua Qiao; Koushik Barman; Martin A Edwards; Alberto F Garrido-Castro; Justine N deGruyter; Hugh Nakamura; Kyle Knouse; Chuanguang Qin; Khalyd J Clay; Denghui Bao; Chao Li; Jeremy T Starr; Carmen Garcia-Irizarry; Neal Sach; Henry S White; Matthew Neurock; Shelley D Minteer; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-02       Impact factor: 15.419

5.  Chemoselective Electrosynthesis Using Rapid Alternating Polarity.

Authors:  Yu Kawamata; Kyohei Hayashi; Ethan Carlson; Shobin Shaji; Dirk Waldmann; Bryan J Simmons; Jacob T Edwards; Christoph W Zapf; Masato Saito; Phil S Baran
Journal:  J Am Chem Soc       Date:  2021-10-01       Impact factor: 16.383

6.  A convenient approach to difluoromethylated all-carbon quaternary centers via Ni(ii)-catalyzed enantioselective Michael addition.

Authors:  Xuan Yu; Hui Bai; Dong Wang; Zhaohai Qin; Jia-Qi Li; Bin Fu
Journal:  RSC Adv       Date:  2018-05-25       Impact factor: 3.361

7.  Academia-industry symbiosis in organic chemistry.

Authors:  Quentin Michaudel; Yoshihiro Ishihara; Phil S Baran
Journal:  Acc Chem Res       Date:  2015-02-23       Impact factor: 22.384

8.  A scalable and operationally simple radical trifluoromethylation.

Authors:  Joel W Beatty; James J Douglas; Kevin P Cole; Corey R J Stephenson
Journal:  Nat Commun       Date:  2015-08-10       Impact factor: 14.919

Review 9.  Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method.

Authors:  Evan J Horn; Brandon R Rosen; Phil S Baran
Journal:  ACS Cent Sci       Date:  2016-05-05       Impact factor: 14.553

10.  The crystalline sponge method updated.

Authors:  Manabu Hoshino; Anupam Khutia; Hongzhu Xing; Yasuhide Inokuma; Makoto Fujita
Journal:  IUCrJ       Date:  2016-02-12       Impact factor: 4.769

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.