Issue 97, 2021

Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion

Abstract

An efficient Rh(III)-catalyzed straightforward strategy is developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp3) C–H functionalization. The method is mild, simple and regioselective with various ring sizes and has good functional group tolerance. The method proceeds via C8-methyl metalation, metal–carbene formation and a subsequent migratory insertion. High dilution is not necessary for this macrocyclization and the only byproduct is nitrogen. A preliminary investigation shows that the C–H metalation step is the rate-determining step.

Graphical abstract: Rh(iii)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion

Supplementary files

Article information

Article type
Communication
Submitted
11 Mha 2021
Accepted
09 Huk 2021
First published
09 Huk 2021

Chem. Commun., 2021,57, 13134-13137

Rh(III)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles via migratory insertion

B. Ghosh, S. Bera, P. Ghosh and R. Samanta, Chem. Commun., 2021, 57, 13134 DOI: 10.1039/D1CC04418D

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