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Synthesis of a (piperazin-1-ylmethyl)biaryl library via microwave-mediated Suzuki–Miyaura cross-couplings

Baltus, Christine and Spencer, John and Clegg, William and Press, Neil and Harrington, Ross (2011) Synthesis of a (piperazin-1-ylmethyl)biaryl library via microwave-mediated Suzuki–Miyaura cross-couplings. Tetrahedron Letters, 52 (31). pp. 3963-3968. ISSN 0040-4039

Abstract

A library of (piperazin-1-ylmethyl)biaryls has been synthesized from tert-butyl 4-(3- and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylates. The resulting boronic acid pinacol esters can react in a Suzuki coupling with arylbromides such as 1-bromo-2-, 3- or 4-nitrobenzene or 2-bromo-5-nitropyridine to form the corresponding biaryls. Judicial removal of the protecting group on the piperazine or facile reduction of the nitro group in the biaryl system enables the manipulation of two points of functionality in order to diversify the scope of the resulting biaryl scaffold.

Item Type: Article
Additional Information: author can archive post-print (ie final draft post-refereeing); Publisher's version/PDF cannot be used
Keywords: Suzuki coupling, biaryl, piperazine, nitro-reduction, microwave, flow chemistry.
Date Deposited: 13 Oct 2015 13:15
Last Modified: 13 Oct 2015 13:15
URI: https://oak.novartis.com/id/eprint/4116

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