188527-50-6Relevant articles and documents
Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines
Chatani, Naoto,Uemura, Takeshi,Asaumi, Taku,Ie, Yutaka,Kakiuchi, Fumitoshi,Murai, Shinji
, p. 755 - 763 (2005)
The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh4(CO)12 results in selective carbonylation at the ortho C-H bond. The reaction is heavily dependent on the solvents used, wi
Ru3(CO)12-Catalyzed Reaction of Pyridylbenzenes with Monoxide and Olefins. Carbonylation at a C-H Bond in the Benzene Ring
Chatani, Naoto,Ie, Yutaka,Kakiuchi, Fumitoshi,Murai, Shinji
, p. 2604 - 2610 (1997)
A ruthenium-catalyzed carbonylation at a C-H bond in a benzene ring is described. The reaction of pyridylbenzenes with CO (20 atm) and ethylene in toluene at 160°C in the presence of a catalytic amount of Ru3(CO)12 results in propionylation at an ortho C-H bond in the benzene ring. Carbonylation does not occur at the pyridine ring, although this is necessary as a directing group to promote the reaction. Olefins such as trimethylvinylsilane and tert-butylethylene in place of ethylene can also be used in this reaction, however 1-hexene, cyclohexene, allyltrimethylsilane, styrene, methyl methacrylate, vinyl acetate, triethoxyvinylsilane, and isopropenyltrimethylsilane do not afford the coupling products. Transition metal complexes, other than ruthenium carbonyl, examined thus far, do not show catalytic activity. In the reaction of meto-substituted pyridylbenzenes, such as those having Me, OMe, CF3, and COOMe group at the meta position in the benzene ring, carbonylation takes place at the less hindered C-H bond exclusively, irrespective of the electronic nature of the substituents. It is apparent that steric factors are more important for the control of regioselectivity. The reaction is also applicable to naphthyl and thienyl rings. Six-membered heterocycles, such as 2-pyrimidine and 4-pyrimidine, are also effective directing groups for carbonylation at a C-H bond in the benzene ring. The present reaction represents the first, effective catalytic carbonylation reaction involving cleavage of the benzene C-H bond.
Silver catalyzed pyridine-directed acceptorless dehydrogenation of secondary alcohols
Zhuang, Xin,Tao, Jing,Luo, Zhen,Hong, Chuan-Ming,Liu, Zheng-Qiang,Li, Qing-Hua,Ren, Li-Qing,Luo, Qun-Li,Liu, Tang-Lin
, p. 245 - 249 (2021/02/03)
A silver catalyzed pyridine-directed acceptorless dehydrogenation of secondary benzyl alcohols was developed. This general procedure delivers ketones with high atom-economy and hydrogen was the sole byproduct. This dehydrogenation reaction has a good functional group tolerance and high efficiency (up to 90% yield and 10,000/1 substrates-to-catalyst ratio).
Ag1Pd1-rGO nanocomposite as recyclable catalyst for CDC reactions of 2-arylpyridines with aldehydes
Hu, Qiyan,Liu, Xiaowang,Huang, Fei,Wang, Feifan,Li, Qian,Zhang, Wu
, p. 27 - 31 (2018/05/29)
Ag1Pd1 nanoparticle-reduced graphene oxide (Ag1Pd1-rGO) nanocomposite was used as an efficient catalyst for the synthesis of aromatic ketones via cross dehydrogenative coupling (CDC) reactions of 2-arylpyridines
