The Solid-Phase Preparation of Biphenyltetrazoles via Suzuki Coupling

N. Cousaert; N. Willand; J.-C. Gesquière; A. Tartar; B. Déprez; R. Deprez-Poulain

doi:10.1055/s-2008-1072793

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Synfacts 2008(6): 0655-0655
DOI: 10.1055/s-2008-1072793

Polymer-Supported Synthesis

The Solid-Phase Preparation of Biphenyltetrazoles via Suzuki Coupling

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
N. Cousaert, N. Willand, J.-C. Gesquière, A. Tartar, B. Déprez, R. Deprez-Poulain*
Université Lille 2 and Institut Pasteur de Lille, France

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Publication History

Publication Date:
21 May 2008 (online)

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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.