Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature

被引:45
|
作者
Klumphu, Piyatida [1 ]
Desfeux, Camille [2 ]
Zhang, Yitao [1 ]
Handa, Sachin [3 ]
Gallou, Fabrice [4 ]
Lipshutz, Bruce H. [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
[2] Chim Paris Tech, Paris, France
[3] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
[4] Novartis Pharmaceut, Basel, Switzerland
基金
美国国家科学基金会;
关键词
INTRAMOLECULAR HYDROALKOXYLATION; EFFICIENT CYCLOISOMERIZATION; GOLD(I) COMPLEXES; HYDROAMINATION; HYDRATION; HYDROXYALLENES; CYCLIZATION; COUPLINGS; ALLENES;
D O I
10.1039/c7sc02405c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several ppm level gold-catalyzed reactions enabled by the ligand HandaPhos can be performed at room temperature in aqueous nanoreactors composed of the surfactant Nok. Variously substituted allenes undergo cycloisomerization leading to heterocyclic products in good yields. Likewise, cyclodehydration is also illustrated under similar conditions, as is an intermolecular variant, hydration of terminal alkynes. Recycling of the catalyst and reaction medium is also illustrated. A low E factor associated with limited solvent use and therefore, waste generation, documents the greenness of this process.
引用
收藏
页码:6354 / 6358
页数:5
相关论文
共 29 条
  • [21] C(sp2)-O Bond Formation through a Nickel-Catalyzed Cross-Coupling Reaction in Water Enabled by Micellar Catalysis
    Ahanthem, Dini
    Laitonjam, Warjeet S.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (10) : 1492 - 1497
  • [22] Selective Reduction of Nitroarenes Catalyzed by Sustainable and Reusable DNA-supported Nickel Nanoparticles in Water at Room Temperature
    Niakan, Mahsa
    Asadi, Zahra
    CATALYSIS LETTERS, 2019, 149 (08) : 2234 - 2246
  • [23] Selective Reduction of Nitroarenes Catalyzed by Sustainable and Reusable DNA-supported Nickel Nanoparticles in Water at Room Temperature
    Mahsa Niakan
    Zahra Asadi
    Catalysis Letters, 2019, 149 : 2234 - 2246
  • [24] Oxidation and Oxidative Bromination Reactions Catalyzed By a Reusable Polymer-Anchored Iron(III) Complex in Water at Room Temperature
    Sk. Manirul Islam
    Kajari Ghosh
    Anupam Singha Roy
    Noor Salam
    Tanmay Chatterjee
    Journal of Inorganic and Organometallic Polymers and Materials, 2014, 24 : 457 - 467
  • [25] Oxidation and Oxidative Bromination Reactions Catalyzed By a Reusable Polymer-Anchored Iron(III) Complex in Water at Room Temperature
    Islam, Sk Manirul
    Ghosh, Kajari
    Roy, Anupam Singha
    Salam, Noor
    Chatterjee, Tanmay
    JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2014, 24 (02) : 457 - 467
  • [26] Mild and Rapid Light-Driven Suzuki-Miyaura Reactions Catalyzed by AuPd Nanoparticles in Water at Room Temperature
    Nazar de Souza, Ana Paula
    de Souza Tomaso, Luiz Phelipe
    da Silva, Vitor Alexandre S.
    da Silva, Gabriel Francisco S.
    Santos, Evelyn C. S.
    Baeta, Eustaquio de S.
    de Campos, Jose Brant
    Carvalho, Nakedia M. F.
    Malta, Luiz Fernando B.
    Senra, Jaqueline D.
    CHEMISTRYOPEN, 2022, 11 (12)
  • [27] C-C Bond Formation via Copper-Catalyzed Conjugate Addition Reactions to Enones in Water at Room Temperature
    Lipshutz, Bruce H.
    Huang, Shenlin
    Leong, Wendy Wen Yi
    Zhong, Guofu
    Isley, Nicholas A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (49) : 19985 - 19988
  • [28] (DHQD)2PHAL ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition reactions in water at room temperature
    Ali, Abdul Aziz
    Chetia, Mitali
    Saikia, Prakash J.
    Sarma, Diganta
    RSC ADVANCES, 2014, 4 (110): : 64388 - 64392
  • [29] The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki-Miyaura Reactions at Room Temperature
    Chen, Wei
    Lu, Xiao-Yan
    Xu, Bei-Hua
    Yu, Wei-guo
    Zhou, Zi-niu
    Hu, Ying
    SYNTHESIS-STUTTGART, 2018, 50 (07): : 1499 - 1510