A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Abstract

An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Keywords

quinolines - palladium catalysis - Heck coupling - deuterated quinolines - iodoanilines

Publication History

Received: 12 July 2021

Accepted after revision: 17 August 2021

Accepted Manuscript online:
17 August 2021

Article published online:
13 October 2021

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