NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles

被引：128

作者：

Park, Jong Hyub

Bhilare, Sachin V.

Youn, So Won ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

关键词：

NUCLEOPHILIC CARBENES; AROMATIC-ALDEHYDES; IODOBENZOIC ACID; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; CARBOXYLIC-ACIDS; COPPER-FREE; ISOCOUMARINS; EFFICIENT; ESTERIFICATION;

D O I：

10.1021/ol200481u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile as been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.

引用

收藏

页码：2228 / 2231

页数：4

相关论文

共 53 条

[1] ISOCOUMARINS - DEVELOPMENTS SINCE 1950 [J].

BARRY, RD .

CHEMICAL REVIEWS, 1964, 64 (03) :229-+

[2] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].

Bellina, F ;

Ciucci, D ;

Vergamini, P ;

Rossi, R .

TETRAHEDRON, 2000, 56 (16) :2533-2545

[3] Intermolecular N-Heterocyclic Carbene Catalyzed Hydroacylation of Arynes [J].

Biju, Akkattu T. ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) :9761-9764

[4] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes [J].

Biju, Akkattu T. ;

Wurz, Nathalie E. ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5970-+

[5]

Castells J., 1977, Tetrahedron Lett, V18, P205, DOI DOI 10.1016/S0040-4039(01)92589-4

[6] Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes [J].

Chan, A ;

Scheidt, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4558-4559

[7] 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

[8] Copper-Free Palladium-Catalyzed Sonogashira Coupling-Annulation: Efficient One-Pot Synthesis of Functionalized Pyrano[4,3-b]quinolines from 2-Chloro-3-formylquinolines [J].

Chandra, Atish ;

Singh, Bhawana ;

Khanna, Ranjana S. ;

Singh, Radhey M. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5664-5666

[9] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].

Chow, KYK ;

Bode, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127

[10] The first tandem acetalization/5-exo-dig cyclization of 6-phenylethynylpyrimidine-5-carbaldehydes:: Efficient synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines [J].

Cikotiene, Inga ;

Morkunas, Marius ;

Motiejaitis, Dainius ;

Rudys, Simonas ;

Brukstus, Algirdas .

SYNLETT, 2008, (11) :1693-1697

← 1 2 3 4 5 6 →