Amphoteric Borylketenimines: Versatile Intermediates in the Synthesis of Borylated Heterocycles

Sherif J Kaldas; Kowan T V O'Keefe; Rodrigo Mendoza-Sanchez; Andrei K Yudin

doi:10.1002/chem.201702008

Amphoteric Borylketenimines: Versatile Intermediates in the Synthesis of Borylated Heterocycles

Chemistry. 2017 Jul 21;23(41):9711-9715. doi: 10.1002/chem.201702008. Epub 2017 Jul 6.

Authors

Sherif J Kaldas¹, Kowan T V O'Keefe¹, Rodrigo Mendoza-Sanchez¹, Andrei K Yudin¹

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6, Canada.

PMID: 28475819
DOI: 10.1002/chem.201702008

Abstract

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.

Keywords: boronates; copper catalysis; cyclic peptides; heterocycles; ketenimines.