Direct ortho-arylation of N-phenacylpyridinium bromide by palladium-catalyzed C-H-bond activation.
A novel palladium catalyzed direct ortho-arylation of N-phenacylpyridinium bromide was developed. The amazing N-phenacyl group regioselectively activates the C-H bond of pyridine and automatically departs from the arylated products. A kinetic isotope effect study proved that the reaction went through a C-H-bond activation pathway and 2,6-diphenylpyridine was produced stepwise from 2-phenylpyridine.
Xu
Jimin
J
Key Laboratory of Bioorganic Phosphorus, Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
Cheng
Guolin
G
Su
Deyong
D
Liu
Yantao
Y
Wang
Xinyan
X
Hu
Yuefei
Y
D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry*
C546672:N-phenacylpyridinium bromide; D011725:Pyridines; D011726:Pyridinium Compounds; C058324:2-phenylpyridine; D010165:Palladium