Amphoteric Borylketenimines: Versatile Intermediates in the Synthesis of Borylated Heterocycles

作者:Kaldas Sherif J; O' Keefe Kowan T V; Mendoza Sanchez Rodrigo; Yudin Andrei K
来源:Chemistry - A European Journal, 2017, 23(41): 9711-9715.
DOI:10.1002/chem.201702008

摘要

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.

  • 出版日期2017-7-21