Literature DB >> 30351143

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

Laura K G Ackerman1, Jesus I Martinez Alvarado1, Abigail G Doyle1.   

Abstract

A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

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Year:  2018        PMID： 30351143      PMCID： PMC6411045          DOI： 10.1021/jacs.8b09191

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


  43 in total

1.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Authors:  Keary M Engle; Tian-Sheng Mei; Masayuki Wasa; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2011-12-14       Impact factor: 22.384

2.  Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide.

Authors:  Francisco Juliá-Hernández; Toni Moragas; Josep Cornella; Ruben Martin
Journal:  Nature       Date:  2017-05-03       Impact factor: 49.962

3.  Amide-directed photoredox-catalysed C-C bond formation at unactivated sp3 C-H bonds.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Nature       Date:  2016-10-12       Impact factor: 49.962

4.  Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Authors:  Alexander C Wotal; Daniel J Weix
Journal:  Org Lett       Date:  2012-02-23       Impact factor: 6.005

5.  Hydrogen Atom Transfer by a High-Valent Nickel-Chloride Complex.

Authors:  Prasenjit Mondal; Paolo Pirovano; Ankita Das; Erik R Farquhar; Aidan R McDonald
Journal:  J Am Chem Soc       Date:  2018-01-24       Impact factor: 15.419

6.  Combined effects on selectivity in Fe-catalyzed methylene oxidation.

Authors:  Mark S Chen; M Christina White
Journal:  Science       Date:  2010-01-29       Impact factor: 47.728

7.  Chemical behavior of tungstate solutions. Part 1. A spectroscopic survey of the species involved.

Authors:  Thierry Barré; Laurent Arurault; François X Sauvage
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2005-02       Impact factor: 4.098

8.  Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents.

Authors:  Wen Zhang; Pinhong Chen; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

Review 9.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

10.  Direct arylation of strong aliphatic C-H bonds.

Authors:  Ian B Perry; Thomas F Brewer; Patrick J Sarver; Danielle M Schultz; Daniel A DiRocco; David W C MacMillan
Journal:  Nature       Date:  2018-08-01       Impact factor: 49.962
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  22 in total

1.  Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp3)-H Bonds.

Authors:  Scott M Thullen; Sean M Treacy; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

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.  Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters.

Authors:  Jiang Wang; Brian P Cary; Peyton D Beyer; Samuel H Gellman; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

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.  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

6.  Copper Catalyzed C(sp3)-H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer.

Authors:  Sean M Treacy; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-02-12       Impact factor: 15.419

Review 7.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

8.  Mechanistic basis for tuning iridium hydride photochemistry from H2 evolution to hydride transfer hydrodechlorination.

Authors:  Seth M Barrett; Bethany M Stratakes; Matthew B Chambers; Daniel A Kurtz; Catherine L Pitman; Jillian L Dempsey; Alexander J M Miller
Journal:  Chem Sci       Date:  2020-03-06       Impact factor: 9.825

9.  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

10.  A cross-dehydrogenative C(sp3)-H heteroarylation via photo-induced catalytic chlorine radical generation.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Nat Commun       Date:  2021-06-29       Impact factor: 14.919
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