An inexpensive and highly stable ligand 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine for Mizoroki–Heck and room temperature Suzuki–Miyaura cross-coupling reactions (original) (raw)

A bulky, inexpensive and simple bidentate ligand 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine (1) has been synthesized and characterized. The palladium catalyst was formed by combination of 1 with [Cl 2 Pd(COD)] in a ratio of 1:1, tested in the SuzukieMiyaura and MizorokieHeck cross-coupling reactions. Coupling of a variety of aryl bromides with phenylboronic acid using methanol as solvent at room temperature, or at 60 C, gave generally high yields of coupled products. Coupling of aryl chlorides with organoboron reagent at 110 C in DMF afforded good yields of biaryls under aerobic conditions. This non-phosphorus, air and moisture stable catalyst also displays good activity for MizorokieHeck coupling reaction in methanol at 60 C with various aryl chlorides and bromides.

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