Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates

被引：126

作者：

Belabassi, Yamina ^{[1
]}

Alzghari, Saeed ^{[1
]}

Montchamp, Jean-Luc ^{[1
]}

机构：

[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2008年 / 693卷 / 19期

关键词：

cross-coupling; phosphorus; palladium; heterocycles; aryl halides;

D O I：

10.1016/j.jorganchem.2008.07.020

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino) ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：3171 / 3178

页数：8

共 68 条

[1] New open frameworks based on metal pyridylphosphonates [J].

Ayyappan, P ;

Evans, OR ;

Foxman, BM ;

Wheeler, KA ;

Warren, TH ;

Lin, WB .

INORGANIC CHEMISTRY, 2001, 40 (23) :5954-5961

[2] NICKEL-CATALYZED ARBUZOV REACTION - MECHANISTIC OBSERVATIONS [J].

BALTHAZOR, TM ;

GRABIAK, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26) :5425-5426

[3]

BELABASSI Y, 2006, ENCY REAGENTS ORGANI

[4] Arylation of 6H-dibenzo[c,e][1,2ℷ5]oxaphosphinine 6-oxide [J].

Beletskaya, IP ;

Neganova, EC ;

Veits, YA .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (12) :1782-1786

[5] 3-PYRIDYLPHOSPHONIC ACID [J].

BENNETT, RD ;

BURGER, A ;

VOLK, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (06) :940-940

[6] Palladium-catalyzed phosphorus-carbon bond formation: cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates [J].

Bravo-Altamirano, K ;

Huang, ZH ;

Montchamp, JL .

TETRAHEDRON, 2005, 61 (26) :6315-6329

[7] Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles:: Methodology for the synthesis of allylic H-phosphinates [J].

Bravo-Altamirano, Karla ;

Abrunhosa-Thomas, Isabelle ;

Montchamp, Jean-Luc .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2292-2301

[8] A novel approach to phosphonic acids from hypophosphorous acid [J].

Bravo-Altamirano, Karla ;

Montchamp, Jean-Luc .

TETRAHEDRON LETTERS, 2007, 48 (33) :5755-5759

[9] Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols [J].

Bravo-Altamirano, Karla ;

Montchamp, Jean-Luc .

ORGANIC LETTERS, 2006, 8 (18) :4169-4171

[10] PREPARATION OF AMINOPHENYLPHOSPHONATES, NITROPHENYLPHOSPHONATES, PYRIDYLPHOSPHONATES, AND QUINOLYLPHOSPHONATES UNDER PHOTOSTIMULATION OR METALLIC ASSISTANCE - ACCESS TO CORRESPONDENT AMINOPHOSPHONIC ACIDS [J].

BULOT, JJ ;

ABOUJAOUDE, EE ;

COLLIGNON, N ;

SAVIGNAC, P .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1984, 21 (02) :197-204

← 1 2 3 4 5 6 7 →