A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides

被引：437

作者：

Fors, Brett P. ^{[1
]}

Watson, Donald A. ^{[1
]}

Biscoe, Mark R. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 41期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/ja8055358

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst system based on a new biarylmonophosphine ligand (BrettPhos) that shows excellent reactivity for C-N cross-coupling reactions is reported. This catalyst system enables the use of aryl mesylates as a coupling partner in C-N bond-forming reactions. Additionally, the use of BrettPhos permits the highly selective monoarylation of an array of primary aliphatic amines and anilines at low catalyst loadings and with fast reaction times, including the first monoarylation of methylamine. Lastly, oxidative addition complexes of BrettPhos are included, which provide insight into the origin of reactivity for this system.

引用

页码：13552 / +

页数：4

共 24 条

[1] RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS
AMATORE, C
CARRE, E
JUTAND, A
MBARKI, MA
[J]. ORGANOMETALLICS, 1995, 14 (04) : 1818 - 1826
[2] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles
Anderson, Kevin W.
Tundel, Rachel E.
Ikawa, Takashi
Altman, Ryan A.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6523 - 6527
[3] Palladium-catalyzed amination of aryl nonaflates
Anderson, KW
Mendez-Perez, M
Priego, J
Buchwald, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) : 9563 - 9573
[4] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides
Biscoe, Mark R.
Fors, Brett P.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) : 6686 - +
[5] Electronic effects on the selectivity of Pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: The competitive roles of amine binding and acidity
Biscoe, Mark R.
Barder, Timothy E.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7232 - 7235
[6] Palladium-mediated N-arylation of heterocyclic diamines: Insights into the origin of an unusual chemoselectivity
Cabello-Sanchez, Noemi
Jean, Ludovic
Maddaluno, Jacques
Lasne, Marie-Claire
Rouden, Jacques
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) : 2030 - 2039
[7] Water-mediated catalyst preactivation: An efficient protocol for C-N cross-coupling reactions
Fors, Brett P.
Krattiger, Philipp
Strieter, Eric
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2008, 10 (16) : 3505 - 3508
[8] Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes
Hartwig, John F.
[J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1936 - 1947
[9] Discovery and understanding of transition-metal-catalyzed aromatic substitution reactions
Hartwig, John F.
[J]. SYNLETT, 2006, (09) : 1283 - 1294
[10] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
Huang, XH
Anderson, KW
Zim, D
Jiang, L
Klapars, A
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6653 - 6655

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