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Deaminative coupling of benzylamines and arylboronic acids.

ABSTRACT: A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF₄ that are conventionally used in the preparation of aryl diazonium salts. This unlocked the formation of the corresponding diarylmethanes by forging a new C-C bond in good yields.

SUBMITTER: Sirvinskaite G

PROVIDER: S-EPMC9930926 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Deaminative coupling of benzylamines and arylboronic acids.

Sirvinskaite Giedre G Reisenbauer Julia C JC Morandi Bill B

Chemical science 20230113 7

A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF4 that are conventionally used in the preparation of aryl diazonium salts. This unlocke ...[more]

PMID: 36819866

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