The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound

Yao Liu, Raimon Puig De La Bellacasa, Bo Li, Ana Belén Cuenca, Shih Yuan Liu

Research output: Indexed journal article Articlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)14059-14064
Number of pages6
JournalJournal of the American Chemical Society
Volume143
Issue number35
DOIs
Publication statusPublished - 8 Sept 2021

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