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Issue 16, 2018
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Pd(ii)-Catalyzed [3 + 2] spiroannulation of α-aryl-β-naphthols with alkynes via a C–H activation/dearomatization approach

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Abstract

Readily available α-aryl-β-naphthols undergo a [3 + 2] spiroannulation with internal alkynes upon treatment with a Pd(II) catalyst and an oxidant. This transformation involves sequential C–H activation, alkyne migratory insertion, and naphthol dearomatization, affording highly appealing spirocyclic molecules in high yields with good functional group tolerance. Preliminary results with chiral phosphoramidite ligands indicate that enantioselective variants are feasible for this process.

Graphical abstract: Pd(ii)-Catalyzed [3 + 2] spiroannulation of α-aryl-β-naphthols with alkynes via a C–H activation/dearomatization approach

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Supplementary files

Article information


Submitted
23 Jun 2018
Accepted
06 Jul 2018
First published
10 Jul 2018

Org. Chem. Front., 2018,5, 2453-2457
Article type
Research Article

Pd(II)-Catalyzed [3 + 2] spiroannulation of α-aryl-β-naphthols with alkynes via a C–H activation/dearomatization approach

L. Han, H. Wang and X. Luan, Org. Chem. Front., 2018, 5, 2453
DOI: 10.1039/C8QO00614H

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