Reductive N-Arylethylation of Aromatic Amines and N-Heterocycles with Enol Ethers

被引：6
作者：
Voegerl, Katharina [1 ]
Ong, Duc Nghia [1 ]
Bracher, Franz [1 ]
机构：
[1] Ludwig Maximilians Univ Munchen, Dept Pharm, Ctr Drug Res, Butenandtstr 5-13, D-81377 Munich, Germany
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 06期
关键词：
arylethylation; triethylsilane; aromatic amines; heterocycles; chemoselectivity; TERTIARY-AMINES; ALKYLATION; AMINATION; INDOLES; DERIVATIVES; COMPLEXES; ALCOHOLS; SYSTEM; AGENTS; ACIDS;
D O I：
10.1055/s-0036-1591859
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient method for N-arylethylation of aromatic amines and heterocycles under mild reductive conditions was developed using (2-methoxyvinyl)(hetero)arenes as building blocks and triethylsilane/trifluoroacetic acid as reducing agent. This protocol is compatible with numerous functional groups, and aliphatic amines are inert due to protonation.
引用
收藏
页码：1323 / 1330
页数：8
相关论文
共 32 条
  • [1] A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes
    Abdel-Magid, Ahmed F.
    Mehrman, Steven J.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) : 971 - 1031
  • [2] POTENTIAL ANTI-ATHEROSCLEROTIC AGENTS .2. (ARALKYLAMINO)BENZOIC AND (ALKYLAMINO)BENZOIC ACID ANALOGS OF CETABEN
    ALBRIGHT, JD
    DEVRIES, VG
    LARGIS, EE
    MINER, TG
    REICH, MF
    SCHAFFER, SA
    SHEPHERD, RG
    UPESLACIS, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (10) : 1378 - 1393
  • [3] A MILD AND SELECTIVE C-3 REDUCTIVE ALKYLATION OF INDOLES
    APPLETON, JE
    DACK, KN
    GREEN, AD
    STEELE, J
    [J]. TETRAHEDRON LETTERS, 1993, 34 (09) : 1529 - 1532
  • [4] Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity
    Brown, Carla E.
    McNulty, James
    Bordon, Claudia
    Yolken, Robert
    Jones-Brando, Lorraine
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (25) : 5951 - 5955
  • [5] Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen
    Cabrero-Antonino, Jose R.
    Adam, Rosa
    Junge, Kathrin
    Beller, Matthias
    [J]. CHEMICAL SCIENCE, 2017, 8 (09) : 6439 - 6450
  • [6] HETEROCYCLIC FREE-RADICALS .8. INFLUENCE OF STRUCTURE AND CONFORMATION OF SIDE-CHAIN ON PROPERTIES OF PHENOTHIAZINE CATION-RADICALS SUBSTITUTED AT NITROGEN
    CLARKE, D
    GILBERT, BC
    HANSON, P
    KIRK, CM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (10): : 1103 - 1110
  • [7] EGGLER JF, 1988, Patent No. 4738972
  • [8] REARRANGEMENTS OF ORGANMETALLIC COMPOUNDS .24. CARBON-SKELETAL [1,2] ANIONIC REARRANGEMENTS OF TERTIARY BENZYLIC AMINES - GEOMETRIC AND ELECTRONIC REQUIREMENTS FOR GENERATING THE SPIROAZACYCLOPROPANE INTERMEDIATE
    EISCH, JJ
    DUA, SK
    KOVACS, CA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) : 4437 - 4444
  • [9] LIGHT-INDUCED REACTIONS OF 2-(N-ALKYL-N-ARYLAMINO)CYCLOHEXANONES AND RELATED AMINO-CYCLOALKANONES - FORMATION OF 7-AZABICYCLO[4.2.0]OCTAN-1-OLS
    ELHAMAMY, AA
    HILL, J
    TOWNEND, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (03): : 573 - 580
  • [10] Haddou T B, 2014, PLOS ONE, V9
1234