Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

被引:10
|
作者
Shegavi, Mahadev L. [1 ]
Saini, Suresh [1 ]
Bhawar, Ramesh [1 ]
Vishwantha, Meghana Desai [1 ]
Bose, Shubhankar Kumar [1 ]
机构
[1] JAIN, Ctr Nano & Mat Sci CNMS, Jain Global Campus, Bangalore 562112, Karnataka, India
关键词
Alkenes; Alkylboronate esters; beta-Borylation; Copper; Heterogeneous Catalysis; Hydroboration; ALKOXY DIBORON REAGENTS; CROSS-COUPLING REACTIONS; N-HETEROCYCLIC CARBENE; ALKYL-HALIDES BEARING; C-H BORYLATION; ASYMMETRIC HYDROBORATION; CONJUGATE ADDITION; ALKYLBORONIC ESTERS; BUILDING-BLOCKS; LIGAND-FREE;
D O I
10.1002/adsc.202001616
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B(2)pin(2) is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the beta-borylation of alpha,beta-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems.
引用
收藏
页码:2408 / 2416
页数:9
相关论文
共 50 条
  • [11] Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water
    Yang, Ming
    Yu, Yunzi
    Ma, Wenxia
    Feng, Yuqin
    Zhang, Gang
    Wu, Yaqi
    Zhou, Fanyu
    Yang, Yongsheng
    Liu, Dezheng
    RSC ADVANCES, 2022, 12 (16) : 9815 - 9820
  • [12] Nucleophilic borylation of benzyl halides with bis(pinacolato)diboron catalyzed by palladium(0) complexes
    Ishiyama, T
    Oohashi, Z
    Ahiko, T
    Miyaura, N
    CHEMISTRY LETTERS, 2002, (08) : 780 - 781
  • [13] Nickel-catalyzed β-boration of α,β-unsaturated esters and amides with bis(pinacolato)diboron
    Hirano, Koji
    Yorimitsu, Hideki
    Oshima, Koichiro
    ORGANIC LETTERS, 2007, 9 (24) : 5031 - 5033
  • [14] A borylcopper species generated from bis(pinacolato)diboron and its additions to α,β-unsaturated carbonyl compounds and terminal alkynes
    Takahashi, K
    Ishiyama, T
    Miyaura, N
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 625 (01) : 47 - 53
  • [15] CeO2-Nanorods-Catalyzed Protoboration of Alkenes and Alkynes with Bis(pinacolato)diboron
    Bhawar, Ramesh
    Saini, Suresh
    Nagaraju, D. H.
    Bose, Shubhankar Kumar
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (04) : 584 - 593
  • [16] Synthesis of β-boryl-α,β-unsaturated carbonyl compounds via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates
    Takagi, J
    Kamon, A
    Ishiyama, T
    Miyaura, N
    SYNLETT, 2002, (11) : 1880 - 1882
  • [17] Activation of diboron reagents: Catalytic copper-catalyzed borylation of electrophilic alkenes
    Santos, Webster L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [18] Palladium-catalyzed benzylic C-H borylation of alkylbenzenes with bis(pinacolato)diboron or pinacolborane
    Ishiyama, T
    Ishida, K
    Takagi, J
    Miyaura, N
    CHEMISTRY LETTERS, 2001, (11) : 1082 - 1083
  • [19] Iridium-catalyzed ortho-C-H Borylation of Aryl Ketones with Bis(pinacolato)diboron
    Itoh, Hiroshi
    Kikuchi, Takao
    Ishiyama, Tatsuo
    Miyaura, Norio
    CHEMISTRY LETTERS, 2011, 40 (09) : 1007 - 1008
  • [20] Copper/Bisphosphine Catalysts in the Internally Borylative Aminoboration of Unactivated Terminal Alkenes with Bis(pinacolato)diboron
    Kato, Kodai
    Hirano, Koji
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10418 - 10424