Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties

Corentin Rasson; Adrien Stouse; Arnaud Boreux; Virginie Cirriez; Olivier Riant

doi:10.1002/chem.201802023

Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties

Chemistry. 2018 Jul 2;24(37):9234-9237. doi: 10.1002/chem.201802023. Epub 2018 May 30.

Authors

Corentin Rasson¹, Adrien Stouse¹, Arnaud Boreux¹, Virginie Cirriez¹, Olivier Riant¹

Affiliation

¹ Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST), Université catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348, Louvain-la-Neuve, Belgium.

PMID: 29694692
DOI: 10.1002/chem.201802023

Abstract

Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita-Baylis-Hillman (MBH) analogues. The optimal conditions described were shown to be compatible with a wide range of aldehydes and ketones. Unprecedented MBH adducts derived from ketones were efficiently synthesized.

Keywords: Morita-Baylis-Hillman reactions; borylation; copper; domino reactions; homogeneous catalysis.