Biphenylene-substituted ruthenocenylphosphine for Suzuki-Miyaura coupling of aryl chlorides

被引：58

作者：

Hoshi, Takashi ^{[1
]}

Nakazawa, Taichi ^{[2
]}

Saitoh, Ippei ^{[2
]}

Mori, Ayako ^{[1
]}

Suzuki, Toshio ^{[1
]}

Sakai, Jun-ichi ^{[1
]}

Hagiwara, Hisahiro ^{[2
]}

机构：

[1] Niigata Univ, Fac Engn, Niigata 9502181, Japan

[2] Niigata Univ, Grad Sch Sci & Technol, Nishi Ku, Niigata 9502181, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 10期

关键词：

D O I：

10.1021/ol800567q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High activity in the palladium-catalyzed Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for the construction of highly hindered tetra- ortho-substituted biaryls can be achieved in good to excellent yields with low catalyst loadings in short reaction times.

引用

页码：2063 / 2066

页数：4

共 56 条

[1] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15195 - 15201
[2] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3690 - 3693
[3] Ferrocenyl monophosphine ligands: Synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides
Baillie, C
Zhang, LX
Xiao, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7779 - 7782
[4] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
Barder, TE
Walker, SD
Martinelli, JR
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
[5] Synthesis, structural, and electron topographical analyses of a dialkylbiaryl phosphine/arene-ligated palladium(I) dimer: Enhanced reactivity in Suzuki-Miyaura coupling reactions
Barder, TE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) : 898 - 904
[6] Insights into amine binding to biaryl phosphine palladium oxidative addition complexes and reductive elimination from biaryl phosphine arylpalladium amido complexes via density functional theory
Barder, Timothy E.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 12003 - 12010
[7] Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen
Barder, Timothy E.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) : 5096 - 5101
[8] Structural insights into active catalyst structures and oxidative addition to (biaryl)phosphine - Palladium complexes via density functional theory and experimental studies
Barder, Timothy E.
Biscoe, Mark R.
Buchwald, Stephen L.
[J]. ORGANOMETALLICS, 2007, 26 (09) : 2183 - 2192
[9] Benchtop monitoring of reaction progress via visual recognition with a handheld UV lamp: In situ monitoring of boronic acids in the Suzuki-Miyaura reaction
Barder, Timothy E.
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2007, 9 (01) : 137 - 139
[10] Palladium-catalyzed cross-coupling between vinyl halides and tert-butyl carbazate:: First general synthesis of the unusual N-Boc-N-alkenylhydrazines
Barluenga, Jose
Moriel, Patricia
Aznar, Fernando
Valdes, Carlos
[J]. ORGANIC LETTERS, 2007, 9 (02) : 275 - 278

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