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The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

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.

SUBMITTER: Liu Y

PROVIDER: S-EPMC9165608 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Liu Yao Y Puig de la Bellacasa Raimon R Li Bo B Cuenca Ana Belén AB Liu Shih-Yuan SY

Journal of the American Chemical Society 20210825 35

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 <b>1</b>, 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 <b>1</b> makes ...[more]

PMID: 34431676

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