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

Arun Kumar Gupta; Chul Yun Rim; Chang Ho Oh

doi:10.1055/s-2004-831303

LETTER

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

Arun Kumar Gupta, Chul Yun Rim, Chang Ho Oh*
GOS Lab, Department of Chemistry, Hanyang University, Sungdong-Gu, Seoul 133-791, Korea
Fax: +82(2)22990762; e-Mail: changho@hanyang.ac.kr;

Abstract

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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

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References

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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.