Abstract
The Pd-catalyzed decarboxylation and dual C(sp3)-H bond functionalization approaches have been described for the preparation of symmetrical and unsymmetrical 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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5005-5020 |
| Number of pages | 16 |
| Journal | Journal of Organic Chemistry |
| Volume | 84 |
| Issue number | 9 |
| DOIs | |
| State | Published - Mar 22 2019 |
| Externally published | Yes |
Bibliographical note
KAUST Repository Item: Exported on 2022-06-10Acknowledgements: C.C.M. appreciates the Science and Engineering Research Board (SERB), New Delhi, and NIT Manipur for financial support in the form of research grant (ECR/2016/000337). We sincerely thank Prof. Anil Kumar, Vikki N. Shinde, and Shiv Dhiman from BITS Pilani for sample analysis and research support. We thank Dr. Chinmoy K. Hazra from King Abdullah University of Science and Technology, KAUST Catalysis Center for sample analysis. We also thank Dodla Sivanageswara Rao from Department of Chemistry, Malaviya National Institute of Technology, Jaipur, for NMR and HRMS analysis. R.G. and N.V. are grateful to the Ministry of Human Resource and Development (MHRD), New Delhi, for fellowship support.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.
ASJC Scopus subject areas
- Organic Chemistry