Selective C-4 alkylation of pyridine by nickel/Lewis acid catalysis.
Direct C-4-selective addition of pyridine across alkenes and alkynes is achieved for the first time by nickel/Lewis acid cooperative catalysis with an N-heterocyclic carbene ligand. A variety of substituents on both alkenes and pyridine are tolerated to give linear 4-alkylpyridines in modest to good yields. The addition across styrene, on the other hand, gives branched 4-alkylpyridines. A single example of C-4-selective alkenylation is also described.
Nakao
Yoshiaki
Y
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan. yoshiakinakao@npc05.mbox.media.kyoto-u.ac.jp
Yamada
Yuuya
Y
Kashihara
Natsuko
N
Hiyama
Tamejiro
T
D000143:Acids / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000143:Acids; D000475:Alkenes; D000480:Alkynes; D008024:Ligands; D009942:Organometallic Compounds; D011725:Pyridines; D009532:Nickel