The Solid-Phase Preparation of Biphenyltetrazoles via Suzuki Coupling

Significance

Solid-phase preparation of bi­phenyltetrazoles was achieved via Suzuki-Miyaura coupling of anchored aryl tetrazoles on PEG-grafted resin (Tentagel S AC). Thus, the reaction of Tentagel S AC and 1 (10 equiv) with Zn(OTf)₂ gave the resin-supported product 2. The Suzuki coupling reaction of 2 and arylboronic acids was carried out in the presence of PdCl₂(dppf) and Na₂CO₃ in aqueous DME to afford the corresponding biphenyltetrazoles 3a-i in 53-80% yields. AT1 receptor antagonist Irbesartan 4 was prepared via solid-phase Suzuki coupling in 64% overall yield.