Synthesis of Selectively Mono-N-Arylated Aliphatic Diamines via Iridium-Catalyzed Amine Alkylation

被引:105
作者
Blank, Benoit [1 ]
Michlik, Stefan [1 ]
Kempe, Rhett [1 ]
机构
[1] Univ Bayreuth, Lehrstuhl Anorgan Chem 2, D-95440 Bayreuth, Germany
关键词
amine alkylation; amino alcohols; diamines; iridium; ASTERISK-IR COMPLEX; BORROWING HYDROGEN; REDUCTIVE AMINATION; TERTIARY-AMINES; ALCOHOLS; SECONDARY; HYDROAMINATION; HETEROCYCLIZATION; ACTIVATION; COORDINATION;
D O I
10.1002/adsc.200900548
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A highly selective phosphorus/nitrogen (P,N) ligand-based iridium catalyst system efficiently catalyzes the reaction of arylamines with unprotected amino alcohols, yielding N-arylated aliphatic diamines in yields of up to 93%. The reaction can be performed with a wide variety of branched and linear amino alcohols in combination with various aminopyridines or substituted anilines.
引用
收藏
页码:2903 / 2911
页数:9
相关论文
共 73 条
[31]  
Gribble GW, 1998, CHEM SOC REV, V27, P395
[32]   Synthesis of primary amines: First homogeneously catalyzed reductive amination with ammonia [J].
Gross, T ;
Seayad, AM ;
Ahmad, M ;
Beller, M .
ORGANIC LETTERS, 2002, 4 (12) :2055-2058
[33]   Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology [J].
Hamid, M. Haniti S. A. ;
Allen, C. Liana ;
Lamb, Gareth W. ;
Maxwell, Aoife C. ;
Maytum, Hannah C. ;
Watson, Andrew J. A. ;
Williams, Jonathan M. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1766-1774
[34]   Borrowing hydrogen in the activation of alcohols [J].
Hamid, Malai Haniti S. A. ;
Slatford, Paul A. ;
Williams, Jonathan M. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1555-1575
[35]   Ruthenium catalysed N-alkylation of amines with alcohols [J].
Hamid, Malai Haniti S. A. ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2007, (07) :725-727
[36]  
HAMID MHS, 2007, EUR J ORG CHEM, V48, P8263
[37]   Development of catalysts for the hydroamination of olefins [J].
Hartwig, JF .
PURE AND APPLIED CHEMISTRY, 2004, 76 (03) :507-516
[38]   Discovery and understanding of transition-metal-catalyzed aromatic substitution reactions [J].
Hartwig, John F. .
SYNLETT, 2006, (09) :1283-1294
[39]   An improved ruthenium catalyst for the environmentally benign amination of primary and secondary alcohols [J].
Hollmann, Dirk ;
Tillack, Annegret ;
Michalik, Dirk ;
Jackstell, Ralf ;
Beller, Matthias .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (03) :403-410
[40]   Non-metallocene rare earth metal catalysts for the diastereoselective and enantioselective hydroamination of aminoalkenes [J].
Hultzsch, KC ;
Gribkov, DV ;
Hampel, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (20) :4441-4452