Ligand-Enabled Sequential C(sp3)-H and C(sp2)-H Diolefination Reaction via Palladium Catalyst
Yangyang Wang1, Xiaobo Xu1, Binghan Pang1
1Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China.
Abstract:
Palladium-catalyzed sequential C(sp3)-H and C(sp2)-H bond diolefination reaction of o-toluidine has been realized for the first time using acetyl-protected aminoethyl phenyl thioether ligands. This novel reaction allows for preparation of the conjugated diene structure via an immediate second olefination on the basis of the first C(sp3)-H olefination in one pot. Various triflyl-protected anilines and acrylates were used as coupling partners elegantly. Furthermore, the unpurified diolefination products can be easily converted to tetrahydroquinoline derivatives.
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