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Synthesis of Previously Inaccessible Borylated Heterocycle Motifs Using Novel Boron‐Containing Amphoteric Molecules
Author(s) -
Trinchera Piera,
Corless Victoria B.,
Yudin Andrei K.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504271
Subject(s) - electrophile , aldehyde , chemistry , nucleophile , alkylation , combinatorial chemistry , molecule , boron , condensation , condensation reaction , organic chemistry , catalysis , physics , thermodynamics
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 CH activation processes.