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Amphoteric Borylketenimines: Versatile Intermediates in the Synthesis of Borylated Heterocycles
Author(s) -
Kaldas Sherif J.,
O'Keefe Kowan T. V.,
MendozaSanchez Rodrigo,
Yudin Andrei K.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702008
Subject(s) - chemistry , regioselectivity , nucleophile , combinatorial chemistry , sulfonyl , catalysis , organic chemistry , alkyl
We report the first synthesis of amphoteric borylketenimines from ethynyl N ‐methyliminodiacetic acid (MIDA) boronate and sulfonyl azides via copper catalysis. In situ trapping of these intermediates with various nucleophiles provided access to novel borylated azetidimines, iminocoumarins, amides, iminooxetanes, and amidines. The described strategy based on borylketenimines offers high levels of chemo‐ and regioselectivity, enabling the synthesis of unprecedented borylated molecules. This work highlights the unexplored utility of borylketenimines in the synthesis of potentially bioactive molecules.