A Facile Synthesis of N-Aryl Substituted Piperidones

被引:2
作者
Geng Qian [1 ]
Zhang Hui [1 ]
Cao Weiguo [1 ,2 ,3 ]
Chen Yali [1 ]
机构
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
N-aryl; 4-piperidone; Ullmann amination; ligand; copper(I) iodide; ONE-POT SYNTHESIS; COUPLING REACTIONS; BOND FORMATION; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; AMINO-ACID; ARYLATION; ULLMANN; IODIDES; HETEROCYCLES;
D O I
10.1002/cjoc.200990335
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and efficient procedure for the synthesis of N-aryl-substituted 4-piperidones was developed. The two step syntheses proceeded with an overall yield of 60%-83% using L-proline as the ligand for the Cu(I)-catalyzed Ullmann amination followed by subsequent hydrolysis of resulting ketals.
引用
收藏
页码:1995 / 2000
页数:6
相关论文
共 48 条
  • [31] Ligand- and base-free copper(II)-catalyzed C-N bond formation: Cross-coupling reactions of organoboron compounds with aliphatic amines and anilines
    Quach, TD
    Batey, RA
    [J]. ORGANIC LETTERS, 2003, 5 (23) : 4397 - 4400
  • [32] Rosiak A, 2007, EUR J ORG CHEM, V2007, P4376
  • [33] Rubiralta M., 1991, Studies in Organic Chemistry, V43, P34, DOI 10.1016/B978-0-444-88348-3.50007-6
  • [34] SCHERER T, 1993, RECL TRAV CHIM PAY B, V112, P535
  • [35] An improved synthesis of N-aryl and N-heteroaryl substituted piperidones
    Schoen, Uwe
    Messinger, Josef
    Buckendahl, M.
    Prabhu, M. S.
    Konda, A.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (14) : 2519 - 2525
  • [36] Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles
    Taillefer, Marc
    Xia, Ning
    Ouali, Armelle
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) : 934 - 936
  • [37] Catalytic imino Diels-Alder reaction by triflic imide and its application to one-pot synthesis from three components
    Takasu, Kiyosei
    Shindoh, Naoya
    Tokuyama, Hidetoshi
    Ihara, Masataka
    [J]. TETRAHEDRON, 2006, 62 (51) : 11900 - 11907
  • [38] TAYLOR EC, 1981, SYNTHESIS-STUTTGART, P606
  • [39] A convenient synthesis to N-aryl-substituted 4-piperidones
    Tortolani, DR
    Poss, MA
    [J]. ORGANIC LETTERS, 1999, 1 (08) : 1261 - 1262
  • [40] Efficient catalysis of Ullmann-type arylation reactions by a novel trinuclear copper(I) complex with a chelating tricarbene ligand
    Tubaro, Cristina
    Biffis, Andrea
    Scattolin, Elena
    Basato, Marino
    [J]. TETRAHEDRON, 2008, 64 (19) : 4187 - 4195