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Metal- and Oxidant-Free Modular Approach To Access N-Alkoxy Oxindoles via Aryne Annulation

Metal- and Oxidant-Free Modular Approach To Access N-Alkoxy Oxindoles via Aryne Annulation

Organic Letters 20(16): 4848-4853

An unprecedented metal- and oxidant-free (intermolecular) approach to access N-alkoxy oxindoles via [3 + 2] cycloadition of in situ generated electrophilic species viz. aryne and (putative) aza-oxyallyl cation is reported. This approach is amenable to both C3-unsubstituted as well as C3-substituted oxindoles. A one-pot manipulation further makes this reaction highly practical. The versatility of this approach was demonstrated through valuable synthetic transformations.

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Accession: 065312254

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PMID: 30044101

DOI: 10.1021/acs.orglett.8b01972

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