N,N-Dimethylformamide (DMF) as a Source of Oxygen To Access α-Hydroxy Arones via the α-Hydroxylation of Arones

被引：38

作者：

Liu, Weibing ^{[1
]}

Chen, Cui ^{[1
]}

Zhou, Peng ^{[1
]}

机构：

[1] Guangdong Univ Petrochem Technol, Coll Chem Engn, 2 Guandu Rd, Maoming 525000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 04期

关键词：

BETA-DICARBONYL COMPOUNDS; KETONES; CYCLIZATION; CATALYST; DERIVATIVES; OXIDATION; SYSTEM;

D O I：

10.1021/acs.joc.6b02751

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented alpha-hydroxylation strategy was developed for the synthesis of alpha-hydroxy arones using N,N-dimethylformamide (DMF) as an oxygen source. Control experiments demonstrated that the oxygen atom of the hydroxy group in the alpha-hydroxy arones produced in this reaction was derived from DMF. This new reaction therefore not only provides an alternative strategy for the a-hydroxylation of arones but also highlights the possibility of using the inexpensive common solvent DMF as a source of oxygen in organic synthesis.

引用

页码：2219 / 2222

页数：4

共 36 条

[1] Cross Dehydrogenative Coupling (CDC) Reactions of N,N-Disubstituted Formamides, Benzaldehydes and Cycloalkanes [J].

Batra, Aanchal ;

Singh, Paramjit ;

Singh, Kamal Nain .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (29) :4927-4947

[2] Reversibility of asymmetric catalyzed C-C bond formation by benzoylformate decarboxylase [J].

Berheide, Marco ;

Kara, Selin ;

Liese, Andreas .

CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (04) :2418-2426

[3] An easy approach to the synthesis of optically active vic-diols: A new single-enzyme system [J].

Bortolini, O ;

Fantin, G ;

Fogagnolo, M ;

Giovannini, PP ;

Guerrini, A ;

Medici, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1854-1856

[4] An Efficient Method for the Synthesis of α-Hydroxyalkyl Aryl Ketones [J].

Chen, Chengqun ;

Feng, Xinghua ;

Zhang, Guozhen ;

Zhao, Qin ;

Huang, Guosheng .

SYNTHESIS-STUTTGART, 2008, (20) :3205-3208

[5] Palladium-Catalyzed Carbonylative Cyclization of Arenes by CH Bond Activation with DMF as the Carbonyl Source [J].

Chen, Jianbin ;

Feng, Jian-Bo ;

Natte, Kishore ;

Wu, Xiao-Feng .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) :16370-16373

[6] Efficient cyclization of tertiary amines and alkenes promoted by KOt-Bu-DMF [J].

Chen, Yan-yan ;

Zhang, Xue-jing ;

Yuan, Hui-min ;

Wei, Wen-tao ;

Yan, Ming .

CHEMICAL COMMUNICATIONS, 2013, 49 (93) :10974-10976

[7] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[8] N,N-Dimethylformamide: A Multipurpose Building Block [J].

Ding, Shengtao ;

Jiao, Ning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (37) :9226-9237

[9] FACILE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS BY ENOLATE OXIDATION WITH DIMETHYLDIOXIRANE [J].

GUERTIN, KR ;

CHAN, TH .

TETRAHEDRON LETTERS, 1991, 32 (06) :715-718

[10] Microwave Energized Synthesis of 2-Aroylindole Derivatives: Piperidine/DMF as an Effective Medium [J].

Haranath, Jayaprakash Soora ;

Balam, Satheesh Krishna ;

Chereddy, Syama Sundar ;

Sthanikam, Siva Prasad ;

Sarva, Santhisudha ;

Gundluru, Mohan ;

Cirandur, Suresh Reddy .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (02) :620-625

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