Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids

Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids 

Daniel M. Allwood *†, David C. Blakemore ‡, Alan D. Brown ‡, and Steven V. Ley †

† Department of Chemistry, University of Cambridge, Cambridge, CB2 1EW, U.K.

‡ Neusentis Chemistry, Pfizer Worldwide Research and Development, The Portway Building, Granta Park, Cambridge, CB21 6GS, U.K.

J. Org. Chem., 2014, 79 (1), pp 328–338

DOI: 10.1021/jo402526z

http://pubs.acs.org/doi/abs/10.1021/jo402526z

The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.