Copper-Catalyzed C-P Coupling through Decarboxylation

被引：224

作者：

Hu, Jie ^{[1
]}

Zhao, Ning ^{[1
]}

Yang, Bin ^{[1
]}

Wang, Ge ^{[1
]}

Guo, Li-Na ^{[1
]}

Liang, Yong-Min ^{[1
]}

Yang, Shang-Dong ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 20期

关键词：

catalysis; copper; C-P coupling; decarboxylation; phosphorus; HECK-TYPE OLEFINATION; BIARYL SYNTHESIS; ARYL BROMIDES; POTASSIUM POLYFLUOROBENZOATES; AROMATIC CARBOXYLATES; H-PHOSPHONATES; BOND FORMATION; AMINO-ACIDS; PHOSPHORUS; LIGANDS;

D O I：

10.1002/chem.201003561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An acid for a phosphine: A versatile protocol for preparation of various di(phenyl)phosphoryl oxides was developed by copper-catalyzed decarboxylative coupling of alkenyl, alkynyl carboxylic acids, and N-benzylproline, respectively, with R2P(O)H (see scheme). All classes of products are important precursors for preparation of biologically active molecules and various phosphorus ligands. This finding represents the first example of copper-catalyzed decarboxylative coupling to construct Cï P bonds. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5516 / 5521

页数：6

共 121 条

[71] Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies [J].

Kalek, Marcin ;

Jezowska, Martina ;

Stawinski, Jacek .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) :3207-3216

[72] A FREE-RADICAL ADDITION FRAGMENTATION REACTION FOR THE PREPARATION OF VINYL SULFONES AND PHOSPHINE OXIDES [J].

KECK, GE ;

BYERS, JH ;

TAFESH, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1127-1128

[73] POLYTERTIARY PHOSPHINES AND ARSINES .1. SYNTHESIS OF POLYTERTIARY PHOSPHINES AND ARSINES BY BASE-CATALYZED ADDITION OF PHOSPHORUS-HYDROGEN AND ARSENIC-HYDROGEN BONDS TO VINYLPHOSPHINES [J].

KING, RB ;

KAPOOR, PN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (17) :4158-&

[74] Palladium- and nickel-catalyzed coupling reactions of α-bromoalkenylphosphonates with arylboronic acids and lithium alkenylborates [J].

Kobayashi, Y ;

William, AD .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1749-1757

[75] P-Heterocycles as Ligands in Homogeneous Catalytic Reactions [J].

Kollar, L. ;

Keglevich, G. .

CHEMICAL REVIEWS, 2010, 110 (07) :4257-4302

[76] Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes [J].

Kondoh, Azusa ;

Yorimitsu, Hideki ;

Oshima, Koichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :4099-4104

[77] Preparation of chiral triarylphosphines by Pd-catalysed asymmetric P-C cross-coupling [J].

Korff, C ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 2004, (05) :530-531

[78]

Leighton C. M., 2006, J AM CHEM SOC, V128, P1446

[79] An efficient synthesis of chiral phosphinyl oxide pyrrolidines and their application to asymmetric direct aldol reactions [J].

Liu, Xue-Wei ;

Le, Thanh Nguyen ;

Lu, Yunpeng ;

Xiao, Yongjun ;

Ma, Jimei ;

Li, Xingwei .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (21) :3997-4003

[80] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands [J].

Martin, Ruben ;

Buchwald, Stephen L. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1461-1473

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