Semi-reduction of alkynes catalyzed by a tri-palladium complex

被引:0
|
作者
Wang, Yu-Hao [1 ]
Liu, Shiuh-Tzung [1 ]
机构
[1] Department of Chemistry, National Taiwan University, Taipei,10617, Taiwan
关键词
D O I
10.1016/j.poly.2024.117276
中图分类号
O62 [有机化学]; TQ [化学工业];
学科分类号
070303 ; 0817 ; 081704 ;
摘要
Upon activation by ammonia-borane, a tri-palladium complex [(bpnp)2Pd3Cl2]Cl2 (Pd3) was found to be catalytically active for hydrogenation of alkynes to render the corresponding cis-olefins. Typically, a mixture of diphenylacetylene (0.80 mmol), Pd3 (0.2 mol %), and NH3.BH3 (10 mol%) in THF/H2O (10:1, 1 mL) was stirred at 30 °C under H2 (1 atm) for 2 h, giving (Z)-stilbene in 95 % yield with a turnover frequency (TOF) ∼240 h−1. This catalyst is applicable to both internal and terminal alkynes with aryl or alkyl substituents. © 2024 Elsevier Ltd
引用
下载
收藏
相关论文
共 50 条
  • [31] Palladium-catalyzed addition of alkynes to cyclopropenes
    Yin, JD
    Chisholm, JD
    CHEMICAL COMMUNICATIONS, 2006, (06) : 632 - 634
  • [32] Palladium-Catalyzed Aminocarbonylation of Alkynes to Succinimides
    Liu, Huizhen
    Lau, Genevieve P. S.
    Dyson, Paul J.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 386 - 391
  • [33] Palladium-Catalyzed Hydroformylation of Alkenes and Alkynes
    Zhang, Yang
    Sigrist, Michel
    Dydio, Pawel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5985 - 5997
  • [34] PALLADIUM-CATALYZED ARYLOXYCARBONYLATION OF TERMINAL ALKYNES
    ITOH, K
    MIURA, M
    NOMURA, M
    TETRAHEDRON LETTERS, 1992, 33 (37) : 5369 - 5372
  • [35] REDUCTION OF PROPARGYLIC ALCOHOL DERIVATIVES CATALYZED BY A ZEROVALENT PALLADIUM COMPLEX
    COLAS, Y
    CAZES, B
    GORE, J
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1987, (01): : 165 - 173
  • [36] Palladium-Catalyzed Intermolecular Aryldifluoroalkylation of Alkynes
    He, Yu-Tao
    Wang, Qiang
    Li, Lian-Hua
    Liu, Xue-Yuan
    Xu, Peng-Fei
    Liang, Yong-Min
    ORGANIC LETTERS, 2015, 17 (21) : 5188 - 5191
  • [37] Palladium-catalyzed phosphinylthiolation of terminal alkynes
    Hoshi, Nobutaka
    Kashiwabara, Taigo
    Tanaka, Masato
    TETRAHEDRON LETTERS, 2012, 53 (16) : 2078 - 2081
  • [38] Palladium-catalyzed hydrophosphinylation of alkenes and alkynes
    Deprèle, S
    Montchamp, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) : 9386 - 9387
  • [39] DI-PALLADIUM(II) AND TRI-PALLADIUM(II) POLYAZACYCLOALKANE COMPLEXES - A CASE OF DEPROTONATED SECONDARY NITROGEN IN SOLUTION AND IN SOLID-STATE
    BENCINI, A
    BIANCHI, A
    DAPPORTO, P
    GARCIAESPANA, E
    MICHELONI, M
    PAOLETTI, P
    PAOLI, P
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (19) : 1382 - 1384
  • [40] Palladium-Catalyzed Arylthiolation of Alkynes Enabled by Surmounting Competitive Dimerization of Alkynes
    Uno, Daisuke
    Nogi, Keisuke
    Yorimitsu, Hideki
    ORGANIC LETTERS, 2019, 21 (20) : 8295 - 8299