A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers

Jones, D. Heulyn and Kay, Steven T. and McLellan, Jayde A. and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2017) A regioselective three component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers. Organic Letters. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.7b01481)

[thumbnail of Jones-etal-OL-2017-A-regioselective-three-component-reaction-of-pyridine-N-oxides]
Preview
 Text. Filename: Jones_etal_OL_2017_A_regioselective_three_component_reaction_of_pyridine_N_oxides.pdf
Accepted Author Manuscript
Download (647kB)| Preview

Abstract

A novel 3-component reaction of pyridine N-oxides, acyl chlorides and cyclic ethers is described. Treatment of an electron defi-cient pyridine N-oxide with an acyl chloride in the presence of a cyclic ether at 25–50 °C leads to a substituted pyridine as a single regioisomer in up to 58% isolated yield. Isotopic labelling experiments and substrate scope support the reaction proceeding through a carbene intermediate.

ORCID iDs

Jones, D. Heulyn, Kay, Steven T. ORCID logoORCID: https://orcid.org/0000-0001-7020-6627, McLellan, Jayde A. ORCID logoORCID: https://orcid.org/0000-0002-3516-4473, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
CORE (COnnecting REpositories)