4.1 Article

Synthesis of Oxygenated ortho-Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening

期刊

CHIMIA
卷 72, 期 12, 页码 870-873

出版社

SWISS CHEMICAL SOC
DOI: 10.2533/chimia.2018.870

关键词

Aryne; Benzaldehydes; Benzocyclobutenols; Cycloaddition; Ring opening

资金

  1. JSPS KAKENHI [JP16H06351]
  2. German Research Foundation (DFG) [MA 7096/1]

向作者/读者索取更多资源

Herein, a two-step procedure for the preparation of oxygenated ortho-methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core via benzyne [2+2] cycloadditions with acetaldehyde lithium enolate to give the corresponding benzocyclobutenols in high yields. Bond-selective ring opening of the benzocyclobutenols under basic conditions in methanol delivers the title compounds.

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