1,2-Addition of Phenylacetylene to Aldimines Catalyzed by InCl3/CuCl in Water under Barbier Conditions

被引：13
|
作者：
Prajapati, Dipak [1 ]
Sarma, Rupam [1 ]
Bhuyan, Debajyoti [1 ]
Hu, Wenhao [2 ]
机构：
[1] CSIR NE Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India
[2] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
来源：
SYNLETT | 2011年 / 05期
关键词：
aldimines; water; indium chloride; copper chloride; propargylamines; ENANTIOSELECTIVE ALKYNE ADDITIONS; AQUEOUS-MEDIA; ORGANIC-REACTIONS; ORGANOMETALLIC REAGENTS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; AROMATIC KETONES; TERMINAL ALKYNES; PROPARGYLAMINES; ALDEHYDES;
D O I：
10.1055/s-0030-1259679
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and efficient method for the preparation of various propargylamines has been achieved by the simple Barbier-Grignard-type reaction of phenylacetylene with a variety of aldimines under aqueous conditions, catalyzed by a bimetallic In-Cu system.
引用
收藏
页码：627 / 630
页数：4
相关论文
共 38 条
  • [1] ASYMMETRIC 1,2-ADDITION OF ORGANOLITHIUMS TO ALDIMINES CATALYZED BY CHIRAL LIGAND
    INOUE, I
    SHINDO, M
    KOGA, K
    TOMIOKA, K
    TETRAHEDRON, 1994, 50 (15) : 4429 - 4438
  • [2] Lipase catalyzed 1,2-addition of thiols to imines under mild conditions
    Albuquerque, Tabata B.
    da Silva, Caren D. G.
    de Oliveira, Aline R.
    dos Santos, Beatriz F.
    da Silva, Beatriz A. L.
    Katla, Ramesh
    Rocha, Mariana P. D.
    Domingues, Nelson L. C.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (03) : 1642 - 1645
  • [3] Thiolysis of alkyl- and aryl-1,2-epoxides in water catalyzed by InCl3
    Fringuelli, F
    Pizzo, F
    Tortoioli, S
    Vaccaro, L
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 379 - 384
  • [4] In/InCl3-mediated 1,2-addition of allyl group to α,β-unsaturated carbonyl compounds
    Kim, HY
    Choi, KI
    Pae, AN
    Koh, HY
    Choi, JH
    Cho, YS
    SYNTHETIC COMMUNICATIONS, 2003, 33 (11) : 1899 - 1904
  • [5] Novel 1,3-dipolar cycloaddition of diazocarbonyl compounds to alkynes catalyzed by InCl3 in water
    Jiang, N
    Li, CJ
    CHEMICAL COMMUNICATIONS, 2004, (04) : 394 - 395
  • [6] A novel InCl3/SiO2-catalyzed hydroarylation of arenes with styrenes under solvent-free conditions
    Sun, Gaojun
    Sun, Huayin
    Wang, Zhiyong
    Zhou, Ming-Ming
    SYNLETT, 2008, (07) : 1096 - 1100
  • [7] FeCl3-Catalyzed 1,2-Addition Reactions of Aryl Aldehydes with Arylboronic Acids
    Zou, Tao
    Pi, Sha-Sha
    Li, Jin-Heng
    ORGANIC LETTERS, 2009, 11 (02) : 453 - 456
  • [8] CATALYZED 1,2-ADDITION VS 1,4-ADDITION OF 3,4-DICHLOROCYCLOBUT-3-ENE-1,2-DIONE WITH UNSATURATED ORGANOSILANES
    OHNO, M
    YAMAMOTO, Y
    EGUCHI, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09): : 2272 - 2273
  • [9] InCl3/SiO2-catalyzed α-amination of 1,3-dicarbonyl compounds under microwave irradiation
    Yadav, JS
    Reddy, BVS
    Venugopal, C
    Padmavani, B
    TETRAHEDRON LETTERS, 2004, 45 (40) : 7507 - 7509
  • [10] InCl3 as an efficient catalyst for cyclotrimerization of aldehydes:: Synthesis of 1,3,5-trioxane under solvent-free conditions
    Elamparuthi, E
    Ramesh, E
    Raghunathan, R
    SYNTHETIC COMMUNICATIONS, 2005, 35 (21) : 2801 - 2804
1234