Regioselective Ring-Opening of Terminal Epoxides Catalyzed by a Porous Metal Silicate Material

被引:0
|
作者
Liu, Yang-Yang [1 ]
Wu, Chuan-De [1 ]
机构
[1] Zhejiang Univ, Dept Chem, State Key Lab Silicon & Adv Semicond Mat, Hangzhou 310027, Peoples R China
基金
中国国家自然科学基金;
关键词
CHEMOSELECTIVE HYDROGENOLYSIS; BIOTECHNOLOGICAL PRODUCTION; STYRENE OXIDE; 2-PHENYLETHANOL; HYDROGENATION; CONVERSION; ALCOHOLS; NANOPARTICLES;
D O I
10.1021/acs.inorgchem.3c03554
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reductive ring-opening of epoxides is a green pathway for synthesizing highly value-added alcohols. In this study, we present a practically applicable approach for the synthesis of anti-Markovnikov-type alcohols with high yields from aliphatic and aromatic epoxides under mild conditions by developing porous metal silicate (PMS) catalysts. A PMS material PMS-20 consists of cobalt and nickel bimetal redox-active sites, exhibiting exceptional catalytic activity and selectivity in the reductive ring-opening of terminal epoxides with >99% yield of primary alcohols. Comparing with the existing methods using noble metals, PMS-20 exhibits broad substrate scope and excellent functional group tolerance by synergistic work between cobalt and nickel species, which is clarified by dual chamber cell system characterization and theoretical calculation results.
引用
收藏
页码:1166 / 1174
页数:9
相关论文
共 50 条
  • [31] Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines
    Cho, CS
    Kim, JH
    Choi, HJ
    Kim, TJ
    Shim, SC
    TETRAHEDRON LETTERS, 2003, 44 (14) : 2975 - 2977
  • [32] Copper-Catalyzed Regioselective Ring-Opening Hydroamination of Methylenecyclopropanes
    Nishikawa, Daiki
    Sakae, Ryosuke
    Miki, Yuya
    Hirano, Koji
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12128 - 12134
  • [33] Enantioselective Ring-Opening Reaction of Epoxides with MeOH Catalyzed by Homochiral Metal-Organic Framework
    Tanaka, Koichi
    Otani, Ken-ichi
    Murase, Takanori
    Nishihote, Shyota
    Urbanczyk-Lipkowska, Zofia
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2012, 85 (06) : 709 - 714
  • [34] Enantioselective ring-opening reaction of epoxides with MeOH catalyzed by homochiral metal-organic framework
    Tanaka, Koichi
    Otani, Ken-Ichi
    Murase, Takanori
    Nishihote, Shyota
    Urbanczyk-Lipkowska, Zofia
    Bulletin of the Chemical Society of Japan, 2012, 85 (06): : 709 - 714
  • [35] Stereo- and regioselective zinc-mediated ring-opening of epoxides with diselenides
    Movassagh, B
    Shamsipoor, M
    SYNLETT, 2005, (08) : 1316 - 1318
  • [36] A HIGHLY REGIOSELECTIVE AND CHEMOSELECTIVE RING-OPENING OF EPOXIDES WITH TRIMETHYLSILYL AZIDE ALUMINUM ISOPROPOXIDE
    EMZIANE, M
    LHOSTE, P
    SINOU, D
    SYNTHESIS-STUTTGART, 1988, (07): : 541 - 544
  • [37] An alternative regioselective ring-opening of epoxides to chlorohydrins mediated by chlorotitanium(IV) reagents
    Nishitani, Kiyoshi
    Shinyama, Kyoko
    Yamakawa, Koji
    HETEROCYCLES, 2007, 74 : 191 - 197
  • [38] Metal-free ring-opening of epoxides with potassium trifluoroborates
    Roscales, Silvia
    Csaky, Aurelio G.
    CHEMICAL COMMUNICATIONS, 2014, 50 (04) : 454 - 456
  • [39] Scandium-catalyzed ring-opening desymmetrization of meso-epoxides
    Ogawa, Chikako
    Wang, Naiwei
    Boudou, Marine
    Azoulay, Stephane
    Manabe, Kei
    Kobayashi, Shu
    HETEROCYCLES, 2007, 72 : 589 - 598
  • [40] Palladium-Catalyzed Ring-Opening Reaction of Cyclopropenones with Vinyl Epoxides
    Lu, Li-Guo
    Chen, Jun-Hua
    Huang, Xiao-Bo
    Liu, Miao-Chang
    Zhou, Yun-Bing
    Wu, Hua-Yue
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16851 - 16859