Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

被引：12
|
作者：
Ong, Derek Yiren [1 ]
Chiba, Shunsuke [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 09期
关键词：
nitriles; aldehydes; sodium hydride; zinc chloride; reduction; AROMATIC NITRILES; CHEMOSELECTIVE REDUCTION; SELECTIVE REDUCTION; ALDEHYDES; CONVERSION; ALCOHOLS; LIGHT;
D O I：
10.1055/s-0039-1690838
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.
引用
收藏
页码：1369 / 1378
页数：10
相关论文
共 50 条
  • [1] PREPARATION OF SODIUM HYDRIDE COMPLEXES OF DIETHYLZINC AND ZINC CHLORIDE
    KOBETZ, P
    BECKER, WE
    INORGANIC CHEMISTRY, 1963, 2 (04) : 859 - +
  • [2] PRODUCTION OF ALDEHYDES BY THE REDUCTION OF NITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE
    ZAKHARKIN, LI
    KHORLINA, IM
    DOKLADY AKADEMII NAUK SSSR, 1957, 116 (03): : 422 - 424
  • [3] REDUCTION OF NITRILES TO PRIMARY AMINES WITH LITHIUM ALUMINUM HYDRIDE
    AMUNDSEN, LH
    NELSON, LS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) : 242 - 244
  • [4] REDUCTION OF POLYFLUOROALKYL NITRILES WITH SODIUM BOROHYDRIDE
    ELLZEY, SE
    WITTMAN, JS
    CONNICK, WJ
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11): : 3945 - &
  • [5] Unexpected Role of Zinc Hydride in Catalytic Hydrosilylation of Ketones and Nitriles
    Boone, Courtney
    Korobkov, Ilia
    Nikonov, Georgii I.
    ACS CATALYSIS, 2013, 3 (10): : 2336 - 2340
  • [6] Hydride Reduction by a Sodium Hydride-Iodide Composite
    Too, Pei Chui
    Chan, Guo Hao
    Tnay, Ya Lin
    Hirao, Hajime
    Chiba, Shunsuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) : 3719 - 3723
  • [7] Zinc Chloride-Catalyzed Expeditious Route to Nitriles
    Paesha, M. A.
    Nizam, Aatika
    SYNTHETIC COMMUNICATIONS, 2010, 40 (09) : 1276 - 1279
  • [8] Copper hydride catalyzed enantioselective conjugate reduction of unsaturated nitriles
    Lee, Daehyung
    Yang, Youngmin
    Yun, Jaesook
    SYNTHESIS-STUTTGART, 2007, (14): : 2233 - 2235
  • [9] THE REDUCTION OF AMIDES TO AMINES VIA NITRILES BY LITHIUM ALUMINUM HYDRIDE
    NEWMAN, MS
    FUKUNAGA, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) : 693 - 696
  • [10] REDUCTION OF QUINOLINE AND ISOQUINOLINE WITH SODIUM HYDRIDE
    NATSUME, M
    KUMADAKI, S
    KANDA, Y
    KIUCHI, K
    TETRAHEDRON LETTERS, 1973, (26) : 2335 - 2338
12345