4.7 Article

Cobalt-catalyzed C(sp2)-H bond imination of phenylalanine derivatives

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 70, Pages 9754-9757

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc02334b

Keywords

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Funding

  1. Latvian Council of Science, project [Cobalt catalyzed C-H bond functionalization] [lzp-2019/1-0220]
  2. European Social Fund [8.2.2.0/20/I/008]
  3. UL foundation [SL-1081-01/2021]

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In this study, we reported a cobalt-catalyzed C-H arylation method using picolinamide as a directing group for phenylalanine derivatives. The reaction displayed good tolerance towards various functional groups and exhibited high yields. The obtained imine products can be easily transformed to 1-aminoisoquinoline derivatives under reductive conditions, providing an attractive alternative. Control experiments suggested that C-H activation might proceed via an electrophilic pathway.
Herein we report the cobalt-catalyzed, picolinamide-directed C-H bond imination protocol of phenylalanine derivatives using isocyanides and a Co(dpm)(2) catalyst. A wide range of functional groups were tolerated under the reaction conditions, yielding imines in high yields. The obtained imine products can easily be transformed to 1-aminoisoquinoline derivatives under reductive conditions, providing an attractive alternative to already existing methodologies. The control experiments indicated that C-H activation might occur via an electrophilic pathway.

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