Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)-H Bond Functionalization

被引:49
作者
Al-Amin, Mohammad [1 ]
Arisawa, Mitsuhiro [1 ]
Shuto, Satoshi [1 ]
Ano, Yusuke [2 ]
Tobisu, Mamoru [2 ]
Chatani, Naoto [2 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[2] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
alkynylation; CH bond functionalization; nanoparticles; palladium; recyclable catalysts; GOLD-SUPPORTED PALLADIUM; C-H FUNCTIONALIZATION; DIRECT ARYLATION; ACTIVATION; ALKENYLATION; ALKYLATION; MOLECULES; OXIDATION; DIOXYGEN;
D O I
10.1002/adsc.201301180
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed a sulfur-modified, gold-supported palladium material (SAuPd) with palladium, Pd, nanoparticles on its surface; it is a recyclable, low-leaching Pd catalyst. Here we report, using SAuPd, the first example of Pd nanoparticle-catalyzed, unactivated C(sp(3))H bond functionalization of amides, using 8-aminoquinoline as a directing group, to yield ethynylated products. The low leaching properties of SAuPd enabled it to be recycled and reused 10 times for C(sp(3))H bond functionalization.
引用
收藏
页码:1631 / 1637
页数:7
相关论文
共 52 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[3]   Development of Second Generation Gold-Supported Palladium Material with Low-Leaching and Recyclable Characteristics in Aromatic Amination [J].
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 .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) :7575-7581
[4]   Suzuki-Miyaura cross-coupling reactions using a low-leaching and highly recyclable gold-supported palladium material and two types of microwave equipments [J].
Al-Amin, Mohammad ;
Akimoto, Masayoshi ;
Tameno, Tsuyoshi ;
Ohki, Yuuta ;
Takahashi, Naoyuki ;
Hoshiya, Naoyuki ;
Shuto, Satoshi ;
Arisawa, Mitsuhiro .
GREEN CHEMISTRY, 2013, 15 (05) :1142-1145
[5]   Ligand-Free Buchwald-Hartwig Aromatic Aminations of Aryl Halides Catalyzed by Low-Leaching and Highly Recyclable Sulfur-Modified Gold-Supported Palladium Material [J].
Al-Amin, Mohammad ;
Honma, Tetsuo ;
Hoshiya, Naoyuki ;
Shuto, Satoshi ;
Arisawa, Mitsuhiro .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) :1061-1068
[6]   Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986
[7]  
Aspin S., 2012, ANGEW CHEM, V124, P10966
[8]   Synthesis of Aromatic α-Aminoesters: Palladium-Catalyzed Long-Range Arylation of Primary Csp3-H Bonds [J].
Aspin, Sam ;
Goutierre, Anne-Sophie ;
Larini, Paolo ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10808-10811
[9]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[10]   A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].
Campeau, LC ;
Rousseaux, S ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021