Expeditious Synthesis of Benzopyrans via Lewis Acid-Catalyzed C−H Functionalization: Remarkable Enhancement of Reactivity by an <i>Ortho</i> Substituent

Keiji Mori, Taro Kawasaki, Shosaku Sueoka, Takahiko Akiyama

Organic Letters · 2010 · 136 citations · 29 references

Concepts

Abstract

An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.

References

29