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- Title
C(sp<sup>2</sup>)−C(sp<sup>2</sup>) Coupling in Water: Palladium(II) Complexes of N-Pincer Tetradentate Porphyrins as Effective Catalysts.
- Authors
Rao, Kanusu Umamaheswara; Appa, Rama Moorthy; Lakshmidevi, Jangam; Vijitha, Raagala; Rao, K. S. V. Krishna; Narasimhulu, Manchala; VENkateswarlu, Katta
- Abstract
A convenient and efficient palladium(II)-porphyrin catalytic system has been developed for the Suzuki-Miyaura cross-coupling (SMC) of aryl bromides with potassium aryltrifluoroborate in water. A series of seven different porphyrins and their complexes with palladium (PdII(por)- 1-PdII(por)- 7) were prepared, and screened their catalytic activity in making biaryls through C(sp2)−C(sp2) coupling. Significantly, the present protocol utilizes safe, water-soluble, and highly stable porphyrins as an alternative to toxic and unstable phosphine ligands. The simple preparation of porphyrins and their complexes, use of moisture-resistant catalyst, excellent yields of the isolated products, use of eco-friendly solvent (such as water), and reusability of the catalyst are the notable advantages of this method. This finding uses marginally explored, moisture-insensitive potassium phenyltrifluoroborates as nucleophiles for SMC. Furthermore, the scope of the method has been demonstrated for the multi-gram scale preparation of biaryls without any side products.
- Subjects
WATER chemistry; PALLADIUM compounds; METAL complexes
- Publication
Asian Journal of Organic Chemistry, 2017, Vol 6, Issue 6, p751
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201700068