Copper-Catalyzed Decarboxylative C-P Cross-Coupling of Alkynyl Acids with H-Phosphine Oxides: A Facile and Selective Synthesis of (E)-1-Alkenylphosphine Oxides

被引：97
作者：
Hu, Gaobo
Gao, Yuxing [1 ]
Zhao, Yufen
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 17期
关键词：
TERMINAL ALKYNES; DIPHENYLPHOSPHINE OXIDE; VINYLPHOSPHINE OXIDES; INTERMOLECULAR HYDROPHOSPHINATION; STEREOSELECTIVE ADDITION; STEREOSPECIFIC CLEAVAGE; TRANSFER HYDROGENATION; CONJUGATE ADDITION; ARYLBORONIC ACIDS; RADICAL-ADDITION;
D O I：
10.1021/ol502009b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.
引用
收藏
页码：4464 / 4467
页数：4
相关论文
共 67 条
[51]   Cu-catalyzed decarboxylative coupling of propiolic acids with boronic acids [J].
Shi, Leilei ;
Jia, Wei ;
Li, Xun ;
Jiao, Ning .
TETRAHEDRON LETTERS, 2013, 54 (15) :1951-1955
[52]   PHOSPHORUS BASED ADDITIVES FOR FLAME-RETARDANT POLYESTER .1. LOW-MOLECULAR WEIGHT ADDITIVES [J].
STACKMAN, RW .
INDUSTRIAL & ENGINEERING CHEMISTRY PRODUCT RESEARCH AND DEVELOPMENT, 1982, 21 (02) :328-331
[53]   Microwave-assisted regioselective addition of P(O)-H bonds to alkenes without added solvent or catalyst [J].
Stockland, RA ;
Taylor, RI ;
Thompson, LE ;
Patel, PB .
ORGANIC LETTERS, 2005, 7 (05) :851-853
[54]   Intermolecular hydrophosphination of alkynes and related carbon-carbon multiple bonds catalyzed by organoytterbiums [J].
Takaki, K ;
Koshoji, G ;
Komeyama, K ;
Takeda, M ;
Shishido, T ;
Kitani, A ;
Takehira, K .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6554-6565
[55]   Intermolecular hydrophosphination of alkynes and related carbon-carbon multiple bonds catalyzed by ytterbium-imine complexes [J].
Takaki, K ;
Takeda, M ;
Koshoji, G ;
Shishido, T ;
Takehira, K .
TETRAHEDRON LETTERS, 2001, 42 (36) :6357-6360
[56]   Copper (II)-catalyzed regio- and stereoselective addition of H/P(O)R2 to alkynes [J].
Trostyanskaya, Inna G. ;
Beletskaya, Irina P. .
TETRAHEDRON, 2014, 70 (15) :2556-2562
[57]   Easy preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3-triazoles by chemoselective trapping of copper(I)-carbon bond with alkoxalyl chloride [J].
Wang, Bo ;
Ahmed, Muhammad Naeem ;
Zhang, Jianlan ;
Chen, Wenwen ;
Wang, Xinyan ;
Hu, Yuefei .
TETRAHEDRON LETTERS, 2013, 54 (45) :6097-6100
[58]   Tandem Reaction of 1-Copper(I) Alkynes for the Synthesis of 1,4,5-Trisubstituted 5-Chloro-1,2,3-triazoles [J].
Wang, Bo ;
Zhang, Jianlan ;
Wang, Xinyan ;
Liu, Nan ;
Chen, Wenwen ;
Hu, Yuefei .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10519-10523
[59]   Experimental and Theoretical Study on Palladium-Catalyzed C-P Bond Formation via Direct Coupling of Triarylbismuths with P(O)-H Compounds [J].
Wang, Tao ;
Sang, Shuai ;
Liu, Liu ;
Qiao, Hongwei ;
Gao, Yuxing ;
Zhao, Yufen .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :608-617
[60]   Cs2CO3-Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides [J].
Wang, Yulei ;
Gan, Jiepeng ;
Liu, Liu ;
Yuan, Hang ;
Gao, Yuxing ;
Liu, Yan ;
Zhao, Yufen .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) :3678-3683
1234567