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Ortho ‐C–H addition of 2‐substituted pyridines with alkenes and imines enabled by mono(phosphinoamido)‐rare earth complexes
Author(s) -
Lin Hailong,
Li Yongrui,
Wang Jinyu,
Zhang Mei,
Jiang Tao,
Li Jing,
Chen Yanhui
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6345
Subject(s) - chemistry , regioselectivity , alkylation , chemoselectivity , catalysis , reagent , pyridine , medicinal chemistry , amine gas treating , surface modification , boron , combinatorial chemistry , organic chemistry
We here reported a special catalytic performance of mono(phosphinoamido)‐ligated rare earth complexes in ortho ‐C–H functionalization of pyridines with nonpolar alkenes and polar imines. Upon treatment with one equiv. of borate reagent B(C 6 F 5 ) 3 or [Ph 3 C][B(C 6 F 5 ) 4 ], complex NP1‐Sc can act as an efficient catalyst for ortho ‐C–H alkylation of pyridines towards alkenes. In the presence of 1:1 mixed secondary amine of HN (SiMe 3 ) 2 and HNBn 2 , complex NP2‐Gd can catalyze ortho ‐C–H addition of pyridines towards imines, effectively. A wide range of substrates were subjected to the catalysis to render the one step synthesis of a variety of ortho ‐alkylated and ortho ‐aminoalkylated pyridine derivatives in good yields and an excellent regioselectivity and chemoselectivity.