Radical acylation: concepts, synthetic applications and directions

被引：17

作者：

Zhang, Yue ^{[1
]}

Zhang, Yili ^{[1
]}

Lin, Jian ^{[4
]}

Li, Zhaodong ^{[2
,3
]}

Huang, Huicai ^{[1
,3
]}

机构：

[1] Guangzhou Univ Chinese Med, Res Ctr Chinese Herbal Resource Sci & Engn, Key Lab Chinese Med Resource Lingnan, Minist Educ, Guangzhou 510006, Peoples R China

[2] South China Agr Univ, Coll Mat & Energy, Guangzhou 510642, Peoples R China

[3] Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

[4] Xiangnan Univ, Coll Chem Biol & Environm Engn, Chenzhou 423000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ALKYL-HALIDES; CARBOXYLIC-ACIDS; KETONE SYNTHESIS; CARBONYL GROUP; NICKEL; ALKENES; ARYL; CYCLIZATION; HYDROACYLATION; CHEMISTRY;

D O I：

10.1039/d2qo01846b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ketones can serve as prevalent structural cores in natural products, pharmaceuticals, and materials science. The synthesis of ketones is one of the most commonly addressed problems in organic chemistry. Radical chemistry has made significant achievements in the last decade, also streamlining the "diversity-oriented" synthesis of functionalized ketones. This review summarizes and comments on progress in the acylation of carbon-centered radical intermediates for ketone synthesis. Reaction scopes, limitations and mechanisms are discussed based on reaction types and catalytic systems. Conclusions and perspectives are also discussed at the end.

引用

页码：1056 / 1085

页数：30

共 126 条

[1] Direct Conversion of Carboxylic Acids to Alkyl Ketones [J].

Amani, Javad ;

Molander, Gary A. .

ORGANIC LETTERS, 2017, 19 (13) :3612-3615

[2] Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides [J].

Amani, Javad ;

Alam, Rauful ;

Badir, Shorouk ;

Molander, Gary A. .

ORGANIC LETTERS, 2017, 19 (09) :2426-2429

[3] Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones [J].

Amani, Javad ;

Sodagar, Esmat ;

Molander, Gary A. .

ORGANIC LETTERS, 2016, 18 (04) :732-735

[4] Mechanism of the nickel-catalyzed electrosynthesis of ketones by heterocoupling of aryl and benzyl halides [J].

Amatore, C ;

Jutand, A ;

Périchon, J ;

Rollin, Y .

MONATSHEFTE FUR CHEMIE, 2000, 131 (12) :1293-1304

[5] Strain energy of small ring hydrocarbons. Influence of C-H bond dissociation energies [J].

Bach, RD ;

Dmitrenko, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4444-4452

[6] Synthesis of Reversed C-Acyl Glycosides through Ni/Photoredox Dual Catalysis [J].

Badir, Shorouk O. ;

Dumoulin, Audrey ;

Matsui, Jennifer K. ;

Molander, Gary A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) :6610-6613

[7] Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation [J].

Bay, Anna, V ;

Farnam, Emelia J. ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (16) :7030-7037

[8] Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones [J].

Bay, Anna, V ;

Fitzpatrick, Keegan P. ;

Gonzalez-Montiel, Gisela A. ;

Farah, Abdikani Omar ;

Cheong, Paul Ha-Yeon ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (33) :17925-17931

[9] Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids [J].

Bay, Anna V. ;

Fitzpatrick, Keegan P. ;

Betori, Rick C. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) :9143-9148

[10]

Bechara WS, 2012, NAT CHEM, V4, P228, DOI [10.1038/NCHEM.1268, 10.1038/nchem.1268]

← 1 2 3 4 5 6 7 8 9 10 →