Issue 2, 2022

Formation of cyclic (boryl)iminomethane derivatives by the insertion of isocyanides into a boron–carbon bond

Abstract

Isocyanides are highly valuable reagents in organic synthesis and have been widely used in multicomponent reactions. Although η2-imidoyl metal complexes, which are important intermediates in isocyanide chemistry, have been extensively explored, their boron species analogues have remained elusive. Hererin, we reported the synthesis of cyclic (boryl)iminomethanes via direct isocyanide insertion into the B–C bond of amino alkenyl boranes in a facile synthetic procedure. A family of well-defined cyclic (boryl)iminomethanes are characterized. Furthermore, the intrinsic ring strain of cyclic (boryl)iminomethanes primes them to further react with isocyanides and selectively afford double insertion products. Our results provide new insights into novel isocyanide chemistry involving boron species.

Graphical abstract: Formation of cyclic (boryl)iminomethane derivatives by the insertion of isocyanides into a boron–carbon bond

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2021
Accepted
02 Dec 2021
First published
03 Dec 2021

Dalton Trans., 2022,51, 741-745

Formation of cyclic (boryl)iminomethane derivatives by the insertion of isocyanides into a boron–carbon bond

H. Zhou, J. Wang, Y. Meng, F. Liu and T. Wang, Dalton Trans., 2022, 51, 741 DOI: 10.1039/D1DT03884B

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