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Metal–free C5‐H Bromination of Quinolines for One‐pot C−X (X=C, O, S) Bond Formations
Author(s) -
Li You,
Zhu Longzhi,
Cao Xin,
Au ChakTong,
Qiu Renhua,
Yin ShuangFeng
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700391
Subject(s) - halogenation , chemistry , aryl , quinoline , amide , alkyl , combinatorial chemistry , solvent , metal , organic chemistry
We developed an efficient and convenient method for metal‐free bromination of 8‐aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. And this bromination step can be followed in a one‐pot manner with five kinds of C−X (X=C, O, S) cross‐coupling reactions without any extra workup, such as removal of the solvent or filtration for the separation of intermediate. The reaction tolerates a wide scope of alkyl and aryl amides as well as (hetero)aryl boronic acids, generating the corresponding arylation products in good to excellent yields. Furthermore, the one‐pot alkenylation, alkynylation, thiolation and phenoxylation of quinolines on the C5 position can be efficiently realized using this brominated quinoline amide molecular platform. Thus, the method shows high practical potential in industrial organic synthesis.