Literature DB >> 33824304

Benzylic C-H acylation by cooperative NHC and photoredox catalysis.

Qing-Yuan Meng1, Lena Lezius1, Armido Studer2.   

Abstract

Methods that enable site selective acylation of sp3 C-H bonds in complex organic molecules are not well explored, particularly if compared with analogous transformations of aromatic and vinylic sp2 C-H bonds. We report herein a direct acylation of benzylic C-H bonds by merging N-heterocyclic carbene (NHC) and photoredox catalysis. The method allows the preparation of a diverse range of benzylic ketones with good functional group tolerance under mild conditions. The reaction can be used to install acyl groups on highly functionalized natural product derived compounds and the C-H functionalization works with excellent site selectivity. The combination of NHC and photoredox catalysis offers options in preparing benzyl aryl ketones.

Entities:  

Year:  2021        PMID: 33824304     DOI: 10.1038/s41467-021-22292-z

Source DB:  PubMed          Journal:  Nat Commun        ISSN: 2041-1723            Impact factor:   14.919


  28 in total

1.  Light-driven, proton-controlled, catalytic aerobic C-H oxidation mediated by a Mn(III) porphyrinoid complex.

Authors:  Heather M Neu; Jieun Jung; Regina A Baglia; Maxime A Siegler; Kei Ohkubo; Shunichi Fukuzumi; David P Goldberg
Journal:  J Am Chem Soc       Date:  2015-04-03       Impact factor: 15.419

Review 2.  Use of solid catalysts in Friedel-Crafts acylation reactions.

Authors:  Giovanni Sartori; Raimondo Maggi
Journal:  Chem Rev       Date:  2006-03       Impact factor: 60.622

3.  Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay.

Authors:  Wen Zhang; Fei Wang; Scott D McCann; Dinghai Wang; Pinhong Chen; Shannon S Stahl; Guosheng Liu
Journal:  Science       Date:  2016-09-02       Impact factor: 47.728

4.  Ruthenium-catalyzed amino- and alkoxycarbonylations with carbamoyl chlorides and alkyl chloroformates via aromatic C-H bond cleavage.

Authors:  Takuya Kochi; Seiya Urano; Hajime Seki; Eiichiro Mizushima; Mitsuo Sato; Fumitoshi Kakiuchi
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

5.  Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds.

Authors:  Sung-Eun Suh; Si-Jie Chen; Mukunda Mandal; Ilia A Guzei; Christopher J Cramer; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419

6.  Light-driven carboxylation of o-alkylphenyl ketones with CO2.

Authors:  Yusuke Masuda; Naoki Ishida; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2015-10-29       Impact factor: 15.419

7.  Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

Authors:  Shuo Guo; Deyaa I AbuSalim; Silas P Cook
Journal:  J Am Chem Soc       Date:  2018-09-24       Impact factor: 15.419

8.  Photocarboxylation of Benzylic C-H Bonds.

Authors:  Qing-Yuan Meng; Tobias E Schirmer; Anna Lucia Berger; Karsten Donabauer; Burkhard König
Journal:  J Am Chem Soc       Date:  2019-07-11       Impact factor: 15.419

9.  Manganese-catalysed benzylic C(sp3)-H amination for late-stage functionalization.

Authors:  Joseph R Clark; Kaibo Feng; Anasheh Sookezian; M Christina White
Journal:  Nat Chem       Date:  2018-04-30       Impact factor: 24.427

10.  Late-stage trifluoromethylthiolation of benzylic C-H bonds.

Authors:  Wentao Xu; Wenliang Wang; Tao Liu; Jin Xie; Chengjian Zhu
Journal:  Nat Commun       Date:  2019-10-25       Impact factor: 14.919

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  14 in total

1.  Single-electron Carbene Catalysis in Redox Processes.

Authors:  Anna V Bay; Karl A Scheidt
Journal:  Trends Chem       Date:  2022-02-11

2.  Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes.

Authors:  Zhijun Zuo; Constantin G Daniliuc; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-25       Impact factor: 16.823

3.  Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation.

Authors:  Anna V Bay; Emelia J Farnam; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2022-03-22       Impact factor: 16.383

4.  Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones.

Authors:  Pengzhi Wang; Keegan P Fitzpatrick; Karl A Scheidt
Journal:  Adv Synth Catal       Date:  2021-12-01       Impact factor: 5.981

5.  Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions*.

Authors:  Ludivine Delfau; Samantha Nichilo; Florian Molton; Julie Broggi; Eder Tomás-Mendivil; David Martin
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-15       Impact factor: 16.823

6.  Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis.

Authors:  Hangyeol Choi; Gangadhar Rao Mathi; Seonghyeok Hong; Sungwoo Hong
Journal:  Nat Commun       Date:  2022-04-01       Impact factor: 17.694

7.  Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis.

Authors:  Hua Huang; Qing-Song Dai; Hai-Jun Leng; Qing-Zhu Li; Si-Lin Yang; Ying-Mao Tao; Xiang Zhang; Ting Qi; Jun-Long Li
Journal:  Chem Sci       Date:  2022-01-21       Impact factor: 9.825

8.  NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones.

Authors:  Lihong Wang; Ruiyang Ma; Jiaqiong Sun; Guangfan Zheng; Qian Zhang
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

9.  Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.

Authors:  Anna V Bay; Keegan P Fitzpatrick; Gisela A González-Montiel; Abdikani Omar Farah; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-14       Impact factor: 16.823

10.  Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.

Authors:  Joshua L Zhu; Karl A Scheidt
Journal:  Tetrahedron       Date:  2021-06-16       Impact factor: 2.388

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