Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts

被引：14

作者：

Dennis, Eric G. ^{[1
,2
]}

Jeffery, David W. ^{[1
]}

Perkins, Michael V. ^{[2
]}

Smith, Paul A. ^{[1
]}

机构：

[1] Australian Wine Res Inst, Glen Osmond, SA 5064, Australia

[2] Univ Adelaide, Sch Chem & Phys Sci, Adelaide, SA 5001, Australia

来源：

TETRAHEDRON | 2011年 / 67卷 / 11期

关键词：

Negishi cross-coupling; Biaryls; Diarylmethanes; Organozinc; Phloroglucinol; Catechin; PALLADIUM-CATALYZED REACTION; SUZUKI-MIYAURA COUPLINGS; BENZYLIC HALIDES; ARYLBORONIC ACIDS; GENERAL-METHOD; STEREOSELECTIVE-SYNTHESIS; ARYL CHLORIDES; BOND FORMATION; DERIVATIVES; ANTIOXIDANT;

D O I：

10.1016/j.tet.2011.01.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several functionalized biaryls and diarylmethanes containing the phloroglucinol subunit were synthesized in 55-85% yields using Negishi cross-couplings of 2,4,6-trimethoxyphenylzinc chloride with aryl and benzyl halides in the presence of catalytic quantities of Pd(DPEPhos)Cl-2. These simple to prepare couplings were generally complete in 1-24 h depending on the halide, and were applicable to aryl and benzyl halides containing both electron-donating and electron-withdrawing groups. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2125 / 2131

页数：7

共 57 条

[1] INTERMOLECULAR AROMATIC SUBSTITUTION BY ARYL NITRENES [J].

ABRAMOVI.RA ;

CHALLAND, SR ;

SCRIVEN, EFV .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (17) :2705-&

[2] Palladium(0)-catalyzed heteroarylation of 2- and 3-indolylzinc derivatives. An efficient general method for the preparation of (2-pyridyl)indoles and their application to indole alkaloid synthesis [J].

Amat, M ;

Hadida, S ;

Pshenichnyi, G ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3158-3175

[3] Synthesis of functionalised diarylmethanes via a cobalt-catalysed cross-coupling of arylzinc species with benzyl chlorides [J].

Amatore, Muriel ;

Gosmini, Corinne .

CHEMICAL COMMUNICATIONS, 2008, (40) :5019-5021

[4] Some applications of the Grignard cross-coupling reaction in the industrial field [J].

Banno, T ;

Hayakawa, Y ;

Umeno, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :288-291

[5] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].

Baudoin, O ;

Cesario, M ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207

[6] Reinvestigation of the noncatalyzed coupling of aryllithium with haloarene: A novel aromatic nucleophilic substitution pathway [J].

Becht, JM ;

Gissot, A ;

Wagner, A ;

Mioskowski, C .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3209-3215

[7] Synthesis of 8-arylated catechin and epicatechin derivatives via Suzuki cross-coupling [J].

Bernini, Roberta ;

Cacchi, Sandro ;

De Salve, Ilse ;

Fabrizi, Giancarlo .

TETRAHEDRON LETTERS, 2007, 48 (29) :4973-4976

[8] Anti-inflammatory acylphloroglucinol derivatives from hops (Humulus lupulus) [J].

Bohr, G ;

Gerhäuser, C ;

Knauft, J ;

Zapp, J ;

Becker, H .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (10) :1545-1548

[9] Synthesis of modified proanthocyanidins:: easy and general introduction of a hydroxy group at C-6 of catechin;: efficient synthesis of elephantorrhizol [J].

Boyer, FD ;

Es-Safi, NE ;

Beauhaire, J ;

Le Guernevé, C ;

Ducrot, PH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :563-566

[10]

Bringmann G, 1999, SYNLETT, P216

← 1 2 3 4 5 6 →