4.8 Article

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

Journal

ORGANIC LETTERS
Volume 12, Issue 8, Pages 1732-1735

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol100316k

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. Grants-in-Aid for Scientific Research [22750044] Funding Source: KAKEN

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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.

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