N-Heterocyclic carbene catalysed aerobic oxidation of aromatic aldehydes to aryl esters using boronic acids

被引：41

作者：

Arde, Panjab ^{[1
]}

Ramanjaneyulu, B. T. ^{[1
]}

Reddy, Virsinha ^{[1
]}

Saxena, Apurv ^{[1
]}

Anand, R. Vijaya ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Sect 81, Manuali 140306, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 04期

关键词：

CARBOXYLIC-ACIDS; ALPHA; BETA-UNSATURATED ALDEHYDES; ESTERIFICATION; ALCOHOLS; CARBONYLATION; CO2;

D O I：

10.1039/c1ob06566a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic behavior of N-heterocyclic carbenes in the aerobic oxidation of aromatic aldehydes to esters with boronic acids has been explored. This transition metal-free protocol allows access to a wide variety of aromatic esters in good to excellent yields under mild reaction conditions.

引用

页码：848 / 851

页数：4

共 55 条

[1] Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid [J].

Barrett, AGM ;

Braddock, DC .

CHEMICAL COMMUNICATIONS, 1997, (04) :351-352

[2]

Beginn U, 2000, CHEM-EUR J, V6, P2016, DOI 10.1002/1521-3765(20000602)6:11<2016::AID-CHEM2016>3.3.CO

[3]

2-J

[4] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[5] Conversion of α,β-unsaturated aldehydes into saturated esters:: An umpolung reaction catalyzed by nucleophilic carbenes [J].

Chan, A ;

Scheidt, KA .

ORGANIC LETTERS, 2005, 7 (05) :905-908

[6] Direct atom-efficient esterification between carboxylic acids and alcohols catalyzed by amphoteric, water-tolerant TiO(acac)2 [J].

Chen, CT ;

Munot, YS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8625-8627

[7]

Chiang P.-C., 2011, TCI MAIL, V149, P2

[8]

Chiang PC, 2011, RSC CATAL SER, P399

[9] On the Role of CO2 in NHC-Catalyzed Oxidation of Aldehydes [J].

Chiang, Pei-Chen ;

Bode, Jeffrey W. .

ORGANIC LETTERS, 2011, 13 (09) :2422-2425

[10] NHC-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Activation [J].

De Sarkar, Suman ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9266-9269

← 1 2 3 4 5 6 →