Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening

Milne, Kirsty and Henry, Martyn C. and Jamieson, Craig (2021) Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening. Tetrahedron Letters, 81. 153344. ISSN 0040-4039 (https://doi.org/10.1016/j.tetlet.2021.153344)

[thumbnail of Milne-etal-TL-2021-Synthesis-of-an-allylic-gem-difluoromethylene-building-block-via-radical-mediated-difluorocyclopropane]
Preview
 Text. Filename: Milne_etal_TL_2021_Synthesis_of_an_allylic_gem_difluoromethylene_building_block_via_radical_mediated_difluorocyclopropane.pdf
Accepted Author Manuscript
License: Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 logo
Download (469kB)| Preview

Abstract

We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-induced cyclopropane ring-opening, operating via an iodide atom transfer reaction.

CORE (COnnecting REpositories)