Hydrogen Atom Transfer-Mediated Cyclisations of Nitriles

Oliver J Turner; John A Murphy; David J Hirst; Eric P A Talbot

doi:10.1002/chem.201805236

Hydrogen Atom Transfer-Mediated Cyclisations of Nitriles

Chemistry. 2018 Dec 12;24(70):18658-18662. doi: 10.1002/chem.201805236. Epub 2018 Nov 12.

Authors

Oliver J Turner^{1

2}, John A Murphy², David J Hirst¹, Eric P A Talbot^{1

3}

Affiliations

¹ GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK.
² Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.
³ Present address: Pharmaron, Hertford Rd, Hoddesdon, EN11 9BU, UK.

PMID: 30341926
DOI: 10.1002/chem.201805236

Abstract

Hydrogen atom transfer-mediated intramolecular C-C coupling reactions between alkenes and nitriles, using PhSiH₃ and catalytic Fe(acac)₃ , are described. This introduces a new strategic bond disconnection for ring-closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

Keywords: cyclization; hydrogen transfer; iron(III); nitriles; radicals.

Grants and funding

GlaxoSmithKline