4.7 Article

Pd-Catalyzed Decarboxylation and Dual C(sp3)-H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 9, Pages 5005-5020

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02971

Keywords

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Funding

  1. Science and Engineering Research Board (SERB), New Delhi
  2. NIT Manipur [ECR/2016/000337]
  3. Ministry of Human Resource and Development (MHRD), New Delhi

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The Pd-catalyzed decarboxylation and dual C(sp(3))-H bond functionalization approaches have been described for the preparation of symmetrical and unsym-metrical 2,4-diarylpyridines. The developed transformations were realized using nonactivated aromatic ketones and amino acids as C-N sources. The efficacy of the catalyst and reagent combination drives the transformation toward the formation of desired products with high yields and selectivity. The described reaction conditions have seduced the self-reaction of phenylalanine via [2 + 2 + 2] cycloaddition and minimized the formation of 3,5-phenylpyridine as a side product, whereas using glycine as a C-N source, the corresponding 2,6-diarylpyridines were formed as minor products.

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