Issue 15, 2023

Formal [4 + 1] cycloadditions of ketiminoboranes and isonitriles

Abstract

A formal [4 + 1] cycloaddition of ketiminoboranes with various isonitriles was developed. Ketiminoboranes were formed by a reaction sequence of hydroboration of a commercially available 1,3-diene with HB(C6F5)2 followed by allylboration of a variety of nitriles. The mechanism involved in situ generated BN-dienes from ketiminoboranes via intramolecular proton transfer, which was supported by deuterium labelling experiments. Additionally, this reaction can be viewed as a catalyst-free multicomponent reaction providing an efficient approach for synthesizing unsaturated BN-heterocycles via the hydroboration/allylboration/[4 + 1] cycloaddition reaction sequence. These results are attractive complements for the [4 + 1] cycloaddition reaction and open up new opportunities for the formation of unsaturated BN-heterocycles beyond traditional five-membered rings.

Graphical abstract: Formal [4 + 1] cycloadditions of ketiminoboranes and isonitriles

Supplementary files

Article information

Article type
Research Article
Submitted
09 Mei 2023
Accepted
20 Jun 2023
First published
22 Jun 2023

Org. Chem. Front., 2023,10, 3837-3842

Formal [4 + 1] cycloadditions of ketiminoboranes and isonitriles

J. Cui and T. Wang, Org. Chem. Front., 2023, 10, 3837 DOI: 10.1039/D3QO00695F

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