DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes

Org Lett. 2020 Dec 18;22(24):9444-9449. doi: 10.1021/acs.orglett.0c03374. Epub 2020 Dec 2.

Abstract

With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the -Br group which can be further transformed to other functionalities by cross-coupling reactions. The modular feature of o-AQM substrates and the simple operation procedures add further advantages to this synthetic method.