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

DOI: 10.1016/j.tetlet.2011.05.025 DOI Help

Authors: John Spencer (Greenwich University) , Christine B. Baltus (University of Greenwich) , Neil J. Press (Novartis Pharmaceuticals UK Ltd) , Ross Harrington (Newcastle University) , William Clegg (Newcastle University)
Co-authored by industrial partner: Yes

Type: Journal Paper
Journal: Tetrahedron Letters , VOL 52 (31) , PAGES 3963 - 3968

State: Published (Approved)
Published: May 2011
Diamond Proposal Number(s): 987

Abstract: Boc-protected (piperazin-1-ylmethyl)biaryls have been synthesised from (Boc-piperazin-1-ylmethyl)phenylboronic acid pinacol esters via a microwave-mediated Suzuki-Miyaura coupling with aryl bromides viz. 1-bromo-, 2-, 3- or 4-nitrobenzene or 2-bromo-5-nitropyridine. Judicial removal of the protecting group on the piperazine, or facile reduction of the nitro group on the biaryl system enabled the manipulation of two points of functionality in order to diversify the scope of the resulting biaryl library.

Journal Keywords: Suzuki–Miyaura Coupling; Biaryl; Piperazine; Microwave

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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