Synlett 2024; 35(08): 915-919
DOI: 10.1055/s-0043-1763618
cluster
Special Issue dedicated to Keith Fagnou

Synergistic Organoboron/Palladium Catalysis for Regioselective N-Allylation of 2-Pyridones, 4-Pyridones, and Related Ambident Heterocycles

Giorgos Yatzoglou
,
Matthew T. Zambri
,
Shrey P. Desai
,
Mark S. Taylor
This work was funded by Natural Sciences and Engineering Research Council of Canada (NSERC, Discovery Grant), the Canada Foundation for Innovation (projects 17545 and 19119), and the Ontario Research Foundation (Province of Ontario).


Abstract

The use of a boronic acid co-catalyst along with a palladium complex enables efficient dehydrative couplings of allylic alcohols and tautomerizable heterocycles. The protocol has been applied to achieve N-allylations of 2-pyridones, 4-pyridones, 4-pyrimidinones, and their benzofused derivatives.

Supporting Information



Publication History

Received: 24 August 2023

Accepted after revision: 04 October 2023

Article published online:
15 November 2023

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