Ru-Catalyzed Decarbonylative Addition of Aliphatic Aldehydes to Terminal Alkynes

被引：48

作者：

Guo, Xiangyu ^{[1
]}

Wang, Jun ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CARBOZINCATION;

D O I：

10.1021/ol101107w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the formation of isolated C=C bonds was developed via a ruthenium-catalyzed decarbonylative addition of aliphatic aldehydes and alkynes. An unprecedented complete switch of chemoselectivity from aromatic aldehydes to aliphatic aldehydes was observed simply by using tri(2,4,6-trismethoxyphenyl)phosphine as ligand. A synthesis by this method of an insect sex pheromone was demonstrated.

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收藏

页码：3176 / 3178

页数：3

相关论文

共 23 条

[1] Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction [J].

Aissa, Christophe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) :1831-1844

[2] Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo .

CHEMICAL REVIEWS, 2009, 109 (08) :3817-3858

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

Beletskaya, IP ;

Cheprakov, AV .

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

[4] Inter- and intramolecular Horner-Wadsworth-Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones [J].

Comins, DL ;

Ollinger, CG .

TETRAHEDRON LETTERS, 2001, 42 (25) :4115-4118

[5]

Dumeunier R., 2004, Modern Carbonyl Olefination

[6] Aldehyde C-H activation with late transition metal organometallic compounds. Formation and reactivity of acyl hydrido complexes [J].

Garralda, Maria A. .

DALTON TRANSACTIONS, 2009, (19) :3635-3645

[7] An Olefination via Ruthenium-Catalyzed Decarbonylative Addition of Aldehydes to Terminal Alkynes [J].

Guo, Xiangyu ;

Wang, Jun ;

Li, Chao-Jun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) :15092-+

[8]

Hoffmann RW, 2001, ANGEW CHEM INT EDIT, V40, P1411, DOI 10.1002/1521-3773(20010417)40:8<1411::AID-ANIE1411>3.0.CO

[9]

2-U

[10] Total synthesis of (±)-phomactin B2 via an intramolecular cyclohexadienone annulation of a chromium carbene complex [J].

Huang, Jie ;

Wu, Chunrui ;

Wulff, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (44) :13366-+