Bidentate phosphines as ligands in the palladium-catalyzed intramolecular arylation: the intermolecular base-assisted proton abstraction mechanism

被引：116

作者：

Pascual, Sergio ^{[1
]}

de Mendoza, Paula ^{[1
]}

Braga, Ataualpa A. C. ^{[1
]}

Maseras, Feliu ^{[1
,2
]}

Echavarren, Antonio M. ^{[1
,3
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[2] Univ Autonoma Barcelona, Unitat Quim Fis, Bellaterra 08193, Catalonia, Spain

[3] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 26期

关键词：

palladium; arylation; phosphines; DFT calculations;

D O I：

10.1016/j.tet.2008.01.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed arylation of aryl bromides can be carried out in the presence of bidentate phosphines, such as dppm, dppe, dppf, and Xantphos under mild conditions. The experimental results and the DFT calculations fully support for this reaction a mechanism proceeding by an intermolecular proton abstraction. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6021 / 6029

页数：9

共 112 条

[1] Synthesis of tricyclic heterocycles via a tandem aryl alkylation/heck coupling sequence [J].

Alberico, Dino ;

Rudolph, Alena ;

Lautens, Mark .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :775-781

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3]

ANSLYN E, 2005, MODERN PHYS ORGANIC, P422

[4] Palladium-catalyzed intramolecular CH arylation of five-membered N-heterocycles [J].

Arai, Nobumichi ;

Takahashi, Masabumi ;

Mitani, Makoto ;

Mori, Atsunori .

SYNLETT, 2006, (18) :3170-3172

[5] Computational approaches to asymmetric synthesis [J].

Balcells, David ;

Maseras, Feliu .

NEW JOURNAL OF CHEMISTRY, 2007, 31 (03) :333-343

[6] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[7] Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen [J].

Barder, Timothy E. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5096-5101

[8] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[9] Silyl, hydrido-silylene, or other bonding modes:: Some unusual structures of [(dhpe)Pt(SIHR2)]+ (dhpe = H2P-CH2-CH2-PH2; R = H, Me, SiH3, Cl, OMe, NMe2) and [(dhpe)Pt(SiR3)]+ (R = Me, Cl) from DFT calculations [J].

Besora, M ;

Maseras, F ;

Lledós, A ;

Eisenstein, O .

INORGANIC CHEMISTRY, 2002, 41 (26) :7105-7112

[10] Preparation of annulated nitrogen-containing heterocycles via a one-pot palladium-catalyzed alkylation/direct arylation sequence [J].

Blaszykowski, C ;

Aktoudianakis, E ;

Bressy, C ;

Alberico, D ;

Lautens, M .

ORGANIC LETTERS, 2006, 8 (10) :2043-2045

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