1,3-Phenylene-bis-(1H)-tetrazole Pincer Ligand for Palladium-Catalyzed Suzuki Cross-Coupling Reactions of Arylhalides with Arylboronic Acids

Abstract

1,3-Phenylene-bis-(1H)-tetrazole pincer ligand was ­synthesized by the reaction of 1, 3-phenylenediamine, sodium azide and triethyl orthoformate in acetic acid and successfully used in ­Suzuki cross coupling reactions of aryl halides with aryl boronic ­acids.

Key words

1,3-phenylene-bis-(1H)-tetrazole pincer ligand - Suzuki cross-coupling reactions - aryl halides

References

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12

General Procedure: Palldium acetate (5 mol%), ligand 2 (5 mol%), and appropriate base (2 equiv) and additive TBAB (10 mol%) were taken in DMF (10 mL) and the mixture was stirred at r.t. for 1 h. Appropriate aryl halides 3a-i (0.1 mol) and arylboronic acids 4a-f (0.11 mmol, 1.1 equiv) were added followed by additional portion of DMF (1.0 mL). The mixture was then stirred at 80-120 °C. The reaction was monitored by TLC. The reaction mixture was cooled, diluted with 20 mL of H₂O and extracted with Et₂O (2 × 20mL). The combined organic portion was washed with brine solution, dried over anhyd MgSO₄, and finally filtered. Evaporatation of the volatiles under reduced pressure to get the corresponding biphenyl products 5.