Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

被引：604

作者：

Hamid, M. Haniti S. A. ^{[1
]}

Allen, C. Liana ^{[1
]}

Lamb, Gareth W. ^{[1
]}

Maxwell, Aoife C. ^{[2
]}

Maytum, Hannah C. ^{[1
]}

Watson, Andrew J. A. ^{[1
]}

Williams, Jonathan M. J. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] GlaxoSmithKline Res & Dev Ltd, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

C BOND FORMATION; DYNAMIC KINETIC RESOLUTION; DIRECT ALPHA-ALKYLATION; PRIMARY ALCOHOLS; SELECTIVE SYNTHESIS; SECONDARY; KETONES; MONOALKYLATION; COMPLEXES; HETEROCYCLIZATION;

D O I：

10.1021/ja807323a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl-2](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. N-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols require more forcing conditions than primary alcohols but are still effective alkylating agents in the presence of this catalyst.

引用

页码：1766 / 1774

页数：9

共 73 条

[41] IODINE-CATALYZED BENZOYLATIONS [J].

KAYE, IA ;

KLEIN, HC ;

BURLANT, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (03) :745-746

[42] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE [J].

KRANENBURG, M ;

VANDERBURGT, YEM ;

KAMER, PCJ ;

VANLEEUWEN, PWNM ;

GOUBITZ, K ;

FRAANJE, J .

ORGANOMETALLICS, 1995, 14 (06) :3081-3089

[43] Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols [J].

Kwon, MS ;

Khn, N ;

Seo, SH ;

Park, IS ;

Cheedrala, RK ;

Park, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6913-6915

[44]

Lamb GW, 2008, CHIM OGGI, V26, P17

[45] Sequential one-pot bimetallic Ir(III)/Pd(0) catalysed mono-/bis-alkylation and spirocyclisation processes of 1,3-dimethylbarbituric acid and allenes [J].

Lofberg, Christian ;

Grigg, Ronald ;

Keep, Ann ;

Derrick, Andrew ;

Sridharan, Visuvanathar ;

Kilner, Colin .

CHEMICAL COMMUNICATIONS, 2006, (48) :5000-5002

[46] Efficient solvent-free selective monoalkylation of arylacetonitriles with mono-, bis-, and tris-primary alcohols catalyzed by a Cp*Ir complex [J].

Lofberg, Christian ;

Grigg, Ronald ;

Whittaker, Mark A. ;

Keep, Ann ;

Derrick, Andrew .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8023-8027

[47] RUTHENIUM CATALYZED-REACTIONS OF ETHYLENE-GLYCOL WITH PRIMARY AMINES - STERIC FACTORS AND SELECTIVITY CONTROL [J].

MARSELLA, JA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 407 (01) :97-105

[48] Easy α-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4 [J].

Martinez, Ricardo ;

Ramon, Diego J. ;

Yus, Miguel .

TETRAHEDRON, 2006, 62 (38) :8988-9001

[49] RuCl2(DMSO)4 catalyzes the β-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process [J].

Martinez, Ricardo ;

Ramon, Diego J. ;

Yus, Miguel .

TETRAHEDRON, 2006, 62 (38) :8982-8987

[50] Convenient synthesis of anionic dinuclear ruthenium(II) complexes [NR2H2][{RuCl(diphosphine)}2(μ-Cl)3] [diphosphine=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 2,2′-bis(di(p-tolyl)phosphino)-1,1′-binaphthyl, and 1,2-bis(diphenylphosphino)benzene]:: crystal structure of [NEt2H2][{RuCl(1,2-bis(diphenylphosphino)benzene)}2(μ-Cl)3] [J].

Mashima, K ;

Nakamura, T ;

Matsuo, Y ;

Tani, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :51-56

← 1 2 3 4 5 6 7 8 →