Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst

被引：21
作者：
Takagi, Koji [1 ]
Fukuda, Hayato [1 ]
Shuto, Satoshi [1 ,4 ]
Otaka, Akira [2 ,3 ]
Arisawa, Mitsuhiro [1 ,5 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[2] Univ Tokushima, Inst Biomed Sci, Tokushima 7708505, Japan
[3] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
[4] Hokkaido Univ, Ctr Res & Educ Drug Discovery, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[5] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650862, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 09期
关键词：
allyl ester; allyl protecting group; cleavage; deprotection; ester; nanoparticle; palladium; GOLD-SUPPORTED PALLADIUM; SIDE-CHAIN; DEPROTECTION; GLYCOPEPTIDES; CARBAPENEMS; DERIVATIVES; ENVIRONMENT; AMINATION; FACILE; ETHERS;
D O I：
10.1002/adsc.201500055
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A safe, facile and low-leaching (up to 0.04 ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.
引用
收藏
页码：2119 / 2124
页数：6
相关论文
共 37 条
  • [1] Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)-H Bond Functionalization
    Al-Amin, Mohammad
    Arisawa, Mitsuhiro
    Shuto, Satoshi
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1631 - 1637
  • [2] Development of Second Generation Gold-Supported Palladium Material with Low-Leaching and Recyclable Characteristics in Aromatic Amination
    Al-Amin, Mohammad
    Arai, Satoshi
    Hoshiya, Naoyoki
    Honma, Tetsuo
    Tamenori, Yusuke
    Sato, Takatoshi
    Yokoyama, Mami
    Ishii, Akira
    Takeuchi, Masashi
    Maruko, Tomohiro
    Shuto, Satoshi
    Arisawa, Mitsuhiro
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) : 7575 - 7581
  • [3] Suzuki-Miyaura cross-coupling reactions using a low-leaching and highly recyclable gold-supported palladium material and two types of microwave equipments
    Al-Amin, Mohammad
    Akimoto, Masayoshi
    Tameno, Tsuyoshi
    Ohki, Yuuta
    Takahashi, Naoyuki
    Hoshiya, Naoyuki
    Shuto, Satoshi
    Arisawa, Mitsuhiro
    [J]. GREEN CHEMISTRY, 2013, 15 (05) : 1142 - 1145
  • [4] Ligand-Free Buchwald-Hartwig Aromatic Aminations of Aryl Halides Catalyzed by Low-Leaching and Highly Recyclable Sulfur-Modified Gold-Supported Palladium Material
    Al-Amin, Mohammad
    Honma, Tetsuo
    Hoshiya, Naoyuki
    Shuto, Satoshi
    Arisawa, Mitsuhiro
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1061 - 1068
  • [5] Formation of self-assembled multi-layer stable palladium nanoparticles for ligand-free coupling reactions
    Arisawa, Mitsuhiro
    Al-Amin, Mohammad
    Honma, Tetsuo
    Tamenori, Yusuke
    Arai, Satoshi
    Hoshiya, Naoyuki
    Sato, Takatoshi
    Yokoyama, Mami
    Ishii, Akira
    Takeguchi, Masaki
    Miyazaki, Tsuyoshi
    Takeuchi, Masashi
    Maruko, Tomohiro
    Shuto, Satoshi
    [J]. RSC ADVANCES, 2015, 5 (01) : 676 - 683
  • [6] Ligand-Free Suzuki-Miyaura Coupling with Sulfur-Modified Gold-Supported Palladium in the Synthesis of a Conformationally-Restricted Cyclopropane Compound Library with Three-Dimensional Diversity
    Arisawa, Mitsuhiro
    Sato, Takatoshi
    Hoshiya, Naoyuki
    Al-Amin, Mohammad
    Kogami, Yuji
    Shuto, Satoshi
    [J]. ACS COMBINATORIAL SCIENCE, 2014, 16 (05) : 215 - 220
  • [7] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis
    Astruc, D
    Lu, F
    Aranzaes, JR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7852 - 7872
  • [8] Astruc D., 2005, Angew. Chem, V117, P8062, DOI DOI 10.1002/ange.200500766
  • [9] Facile and selective cleavage of allyl ethers, amines and esters using polymethylhydrosiloxane-ZnCl2/Pd(PPh3)4
    Chandrasekhar, S
    Reddy, CR
    Rao, RJ
    [J]. TETRAHEDRON, 2001, 57 (16) : 3435 - 3438
  • [10] Corey E. J., 1993, TETRAHEDRON LETT, V34, P6979
1234