title: Synthesis of Previously Inaccessible Borylated Heterocycle Motifs Using Novel Boron-Containing Amphoteric Molecules.
abstract: The photoredox-organocatalyzed α-alkylation of the α-MIDA boryl aldehyde with a range of α-bromoketones resulted in the first examples of boron-containing 1,4-dicarbonyl compounds. These novel trifunctional amphoteric molecules, which bear an additional, strategically placed electrophilic site compared to the starting amphoteric α-boryl aldehyde, were subjected to double-condensation reactions in the presence of various nucleophiles. As a result, a variety of synthetically challenging 3-borylated pyrroles and furans and 4-borylated pyridazines were generated. The borylated regioisomers accessible with this condensation-based strategy are distinctly different from those arising from the well-known lithiation and C-H activation processes.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6 (Canada).
authors.forename: Piera
authors.initials: P
authors.lastname: Trinchera
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6 (Canada).
authors.forename: Victoria B
authors.initials: VB
authors.lastname: Corless
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6 (Canada). ayudin@chem.utoronto.ca.
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D001895:Boron / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D006571:Heterocyclic Compounds; D001895:Boron
keywords: 1,4-dicarbonyl compounds; MIDA boronates; amphoteric molecules; borylated heterocycles; condensation