An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade?

Organic & Biomolecular Chemistry Pub Date: 2021-04-19 DOI: 10.1039/D1OB00430A

Abstract

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles. Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism.

Graphical abstract: An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade
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