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Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

ABSTRACT: We report herein that symmetrical and non-symmetrical N-heterobiaryls are produced by a potassium tert-butoxide-mediated dimerization of heterocyclic N-oxides. The reaction is scalable and transition metal-free, and can be carried out under thermal and microwave conditions. Preliminary mechanistic studies point to the involvement of radical anionic intermediates arising from the N-oxide substrates and potassium tert-butoxide.

SUBMITTER: Stephens DE

PROVIDER: S-EPMC5109978 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Stephens David E DE Lakey-Beitia Johant J Burch Jessica E JE Arman Hadi D HD Larionov Oleg V OV

Chemical communications (Cambridge, England) 20160801 64

We report herein that symmetrical and non-symmetrical N-heterobiaryls are produced by a potassium tert-butoxide-mediated dimerization of heterocyclic N-oxides. The reaction is scalable and transition metal-free, and can be carried out under thermal and microwave conditions. Preliminary mechanistic studies point to the involvement of radical anionic intermediates arising from the N-oxide substrates and potassium tert-butoxide. ...[more]

PMID: 27440397

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