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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期

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

页码：2903 / 2911

页数：9

共 73 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] Amines made easily: A highly selective hydroaminomethylation of olefins [J].

Ahmed, M ;

Seayad, AM ;

Jackstell, R ;

Beller, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10311-10318

[3] SIR97:: a new tool for crystal structure determination and refinement [J].

Altomare, A ;

Burla, MC ;

Camalli, M ;

Cascarano, GL ;

Giacovazzo, C ;

Guagliardi, A ;

Moliterni, AGG ;

Polidori, G ;

Spagna, R .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119

[4]

[Anonymous], ANGEW CHEM

[5] INTERACTION OF LONG OPEN-CHAIN POLYAZAALKANES WITH HYDROGEN AND COPPER(II) IONS [J].

ARAGO, J ;

BENCINI, A ;

BIANCHI, A ;

GARCIAESPANA, E ;

MICHELONI, M ;

PAOLETTI, P ;

RAMIREZ, JA ;

PAOLI, P .

INORGANIC CHEMISTRY, 1991, 30 (08) :1843-1849

[6] N-Heterocyclization of Naphthylamines with 1,2-and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System [J].

Aramoto, Hiroomi ;

Obora, Yasushi ;

Ishii, Yasutaka .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :628-633

[7] Palladium-catalyzed amination in the synthesis of macrocycles comprising cholane, polyamine and pyridine units [J].

Averin, Alexei D. ;

Ranyuk, Elena R. ;

Lukashev, Nikolai V. ;

Golub, Svetlana L. ;

Buryak, Alexel K. ;

Beletskaya, Irina P. .

TETRAHEDRON LETTERS, 2008, 49 (07) :1188-1191

[8] Mechanism of homogeneous iridium-catalyzed alkylation of amines with alcohols from a DFT study [J].

Balcells, David ;

Nova, Ainara ;

Clot, Eric ;

Gnanamgari, Dinakar ;

Crabtree, Robert H. ;

Eisenstein, Odile .

ORGANOMETALLICS, 2008, 27 (11) :2529-2535

[9]

Baxter E.W., 2002, ORGANIC REACTIONS, V59, P1, DOI [DOI 10.1002/0471264180.0R059.01, DOI 10.1002/0471264180.OR059.01]

[10] Palladium(II) co-ordination by linear N-methylated polyamines: a solution and solid-state study [J].

Bazzicalupi, C ;

Bencini, A ;

Cohen, H ;

Giorgi, C ;

Golub, G ;

Meyerstein, D ;

Navon, N ;

Paoletti, P ;

Valtancoli, B .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (10) :1625-1631

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