Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

被引：16

作者：

Wu, Yong ^{[1
]}

Fu, Wai Chung ^{[2
,3
]}

Chiang, Chien-Wei ^{[1
]}

Choy, Pui Ying ^{[2
,3
]}

Kwong, Fuk Yee ^{[2
,3
]}

Lei, Aiwen ^{[1
,4
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

[2] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

[4] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ARYL CHLORIDES; REDUCTIVE ELIMINATION; CARBONYL-COMPOUNDS; PHOSPHINE-LIGANDS; MILD CONDITIONS; ARYLATION; MESYLATES; COMPLEX; METAL; IDENTIFICATION;

D O I：

10.1039/c6cc08392g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of palladium-catalysed selective mono-alpha-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1-1.0 mol%), the reaction provides mono-alpha-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small beta,gamma-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.

引用

页码：952 / 955

页数：4

共 48 条

[41] Preparation of α,β-unsaturated esters and amides via external-CO-free palladium-catalyzed carbonylation of alkenyl tosylates [J].

Ueda, Tsuyoshi ;

Konishi, Hideyuki ;

Manabe, Kei .

TETRAHEDRON LETTERS, 2012, 53 (38) :5171-5175

[42] Identification of a Novel Inhibitor of Dengue Virus Protease through Use of a Virtual Screening Drug Discovery Web Portal [J].

Viswanathan, Usha ;

Tomlinson, Suzanne M. ;

Fonner, John M. ;

Mock, Stephen A. ;

Watowich, Stanley J. .

JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2014, 54 (10) :2816-2825

[43] "Greener" Friedel-Crafts Acylations: A Metal- and Halogen-Free Methodology [J].

Wilkinson, Mark C. .

ORGANIC LETTERS, 2011, 13 (09) :2232-2235

[44] A versatile palladium catalyst system for Suzuki-Miyaura coupling of alkenyl tosylates and mesylates [J].

Wong, Pui Yu ;

Chow, Wing Kin ;

Chung, Kin Ho ;

So, Chau Ming ;

Lau, Chak Po ;

Kwong, Fuk Yee .

CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8328-8330

[45] When cross-coupling partners meet indolylphosphines [J].

Wong, Shun Man ;

Yuen, On Ying ;

Choy, Pui Ying ;

Kwong, Fuk Yee .

COORDINATION CHEMISTRY REVIEWS, 2015, 293 :158-186

[46] P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides [J].

Wong, Shun Man ;

So, Chau Ming ;

Chung, Kin Ho ;

Luk, Chi Him ;

Lau, Chak Po ;

Kwong, Fuk Yee .

TETRAHEDRON LETTERS, 2012, 53 (29) :3754-3757

[47] Practical Direct α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis [J].

Xu, Yan ;

Su, Tianshun ;

Huang, Zhongxing ;

Dong, Guangbin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) :2559-2563

[48] Synthesis of Z-Alkenes from Rh(I)-Catalyzed Olefin Isomerization of β,γ-Unsaturated Ketones [J].

Zhuo, Lian-Gang ;

Yao, Zhong-Ke ;

Yu, Zhi-Xiang .

ORGANIC LETTERS, 2013, 15 (18) :4634-4637

← 1 2 3 4 5 →