Journal
CHIMIA
Volume 72, Issue 12, Pages 870-873Publisher
SWISS CHEMICAL SOC
DOI: 10.2533/chimia.2018.870
Keywords
Aryne; Benzaldehydes; Benzocyclobutenols; Cycloaddition; Ring opening
Categories
Funding
- JSPS KAKENHI [JP16H06351]
- German Research Foundation (DFG) [MA 7096/1]
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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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