4 years ago

Metal–free C5-H Bromination of Quinolines for One-pot C−X (X=C, O, S) Bond Formations

Metal–free C5-H Bromination of Quinolines for One-pot C−X (X=C, O, S) Bond Formations
Shuang-Feng Yin, You Li, Chak-Tong Au, Renhua Qiu, Longzhi Zhu, Xin Cao
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700391

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