Orthogonal selectivity with cinnamic acids in 3-substituted benzofuran synthesis through C-H olefination of phenols

被引：60

作者：

Agasti, Soumitra ^{[1
]}

Sharma, Upendra ^{[1
]}

Naveen, Togati ^{[1
]}

Maiti, Debabrata ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 25期

关键词：

UNACTIVATED INTERNAL ALKYNES; MARINE SPONGE; OXIDATIVE ANNULATION; CARBOXYLIC-ACIDS; ARYL CHLORIDES; HECK REACTIONS; OXIME ESTERS; IANTHELLA SP; O-ARYLATION; INHIBITORS;

D O I：

10.1039/c4cc07026g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium catalyzed intermolecular annulation of cinnamic acids and phenols has been achieved for the selective synthesis of 3-substituted benzofurans. Isotope labeling, competition experiments, kinetic studies, and intermediate trapping have supported a sequence of C-C bond formation and decarboxylation followed by the C-O cyclization pathway.

引用

页码：5375 / 5378

页数：4

共 48 条

[1]

AlvarezBuilla J, 2011, MODERN HETEROCYCLIC CHEMISTRY, VOL 4, P1, DOI 10.1002/9783527637737

[2] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].

Anderson, Kevin W. ;

Ikawa, Takashi ;

Tundel, Rachel E. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695

[3] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[4] Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone [J].

Carlsson, B ;

Singh, BN ;

Temciuc, M ;

Nilsson, S ;

Li, YL ;

Mellin, C ;

Malm, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :623-630

[5] Recyclable copper-catalyst in aqueous media:: O- and N-arylation reactions towards the benzofuroindole framework [J].

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther ;

Tellitu, Imanol .

GREEN CHEMISTRY, 2007, 9 (03) :219-220

[6]

CASIRAGHI G, 1977, SYNTHESIS-STUTTGART, P122

[7] Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation [J].

Cornella, Josep ;

Righi, Marika ;

Larrosa, Igor .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9429-9432

[8] Synthesis and structure-activity studies of novel orally active non-terpenoic 2,3-oxidosqualene cyclase inhibitors [J].

Dehmlow, H ;

Aebi, JD ;

Jolidon, S ;

Ji, YH ;

von der Mark, EM ;

Himber, J ;

Morand, OH .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) :3354-3370

[9] One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization [J].

Flynn, BL ;

Hamel, E ;

Jung, MK .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (12) :2670-2673

[10] Kinetic Isotope Effects in the Study of Organometallic Reaction Mechanisms [J].

Gomez-Gallego, Mar ;

Sierra, Miguel A. .

CHEMICAL REVIEWS, 2011, 111 (08) :4857-4963

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