N-Alkylation of carbamates and amides with alcohols catalyzed by a Cp*Ir complex

被引：68
作者：
Fujita, Ken-ichi [1 ,2 ]
Komatsubara, Atsuo [1 ]
Yamaguchi, Ryohei [1 ]
机构：
[1] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan
[2] Kyoto Univ, Grad Sch Global Environm Studies, Kyoto 6068501, Japan
来源：
TETRAHEDRON | 2009年 / 65卷 / 18期
关键词：
Iridium catalyst; N-Alkylation; Carbamate; Alcohol; DIRECT ALPHA-ALKYLATION; SECONDARY ALCOHOLS; TERTIARY-AMINES; BORROWING HYDROGEN; ORGANIC-SYNTHESIS; RUTHENIUM; EFFICIENT; AMINATION; ACTIVATION; ALDEHYDES;
D O I：
10.1016/j.tet.2009.03.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New atom-economical catalytic systems consisting of [Cp*IrCl2](2)/NaOAc (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of carbamates and amides using alcohols as alkylating agents under solvent-free conditions have been developed. For example, the reaction of n-butyl carbamate with benzyl alcohol in the presence of [Cp*IrCl2](2) (5.0 mol % Ir) and NaOAc (5.0 mol %) at 130 degrees C under the absence of solvent gives n-butyl N-benzylcarbamate in the yield of 94%. The present catalytic system is applicable to not only carbamates but also amides, and only harmless water is produced as co-product. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3624 / 3628
页数：5
相关论文
共 54 条
  • [1] ESTERS OF CARBAMIC ACID
    ADAMS, P
    BARON, FA
    [J]. CHEMICAL REVIEWS, 1965, 65 (05) : 567 - &
  • [2] [Anonymous], 2009, Iridium Complexes in Organic Synthesis, DOI DOI 10.1002/9783527623075.CH5
  • [3] Mechanism of homogeneous iridium-catalyzed alkylation of amines with alcohols from a DFT study
    Balcells, David
    Nova, Ainara
    Clot, Eric
    Gnanamgari, Dinakar
    Crabtree, Robert H.
    Eisenstein, Odile
    [J]. ORGANOMETALLICS, 2008, 27 (11) : 2529 - 2535
  • [4] Reductive BOC-amination of aldehydes
    Bernacka, E
    Klepacz, A
    Zwierzak, A
    [J]. TETRAHEDRON LETTERS, 2001, 42 (30) : 5093 - 5094
  • [5] Borrowing hydrogen: iridium-catalysed reactions for the formation of C-C bonds from alcohols
    Black, PJ
    Cami-Kobeci, G
    Edwards, MG
    Slatford, PA
    Whittlesey, MK
    Williams, JMJ
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 116 - 125
  • [6] An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols
    Blank, Benoit
    Madalska, Martyna
    Kempe, Rhett
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 749 - 758
  • [7] Pleuromutilins. Part 1: The identification of novel mutilin 14-carbamates
    Brooks, G
    Burgess, W
    Colthurst, D
    Hinks, JD
    Hunt, E
    Pearson, MJ
    Shea, B
    Takle, AK
    Wilson, JM
    Woodnutt, G
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (05) : 1221 - 1231
  • [8] N-alkylation of phenethylamine and tryptamine
    Cami-Kobeci, G
    Slatford, PA
    Whittlesey, MK
    Williams, JMJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) : 535 - 537
  • [9] An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling
    Cho, CS
    Kim, BT
    Kim, TJ
    Shim, SC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 9020 - 9022
  • [10] Radical dearomatization of benzene leading to phenanthridine and phenanthridinone derivatives related to (±)-pancratistatin
    Crich, David
    Krishnamurthy, Venkataramanan
    [J]. TETRAHEDRON, 2006, 62 (29) : 6830 - 6840
123456