The Versatile reaction chemistry of an slpha-boryl diazo compound

Autores/as

Liu, Yao; Puig de la Bellacasa, Raimon; Li, Bo; Cuenca, Ana Belén; Liu, Shih-Yuan

Abstract

The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C–H activation, O–H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.

WoS

Scopus

 

Altmetrics

  

 

Publicación

Journal of the American Chemical Society, 8 September 2021, v.143, n.35, p. 14059-14064

Fecha de publicación

2021-09-08

DOI

https://doi.org/10.1021/jacs.1c06112