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

Mark M. Maturi | Zendy; Ken Ohmori | Zendy; Keisuke Suzuki | Zendy

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

Author(s) -

Mark M. Maturi,

Ken Ohmori,

Keisuke Suzuki

Publication year - 2018

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.2018.870

Subject(s) - aryne , chemistry , cycloaddition , regioselectivity , ring (chemistry) , methanol , benzene , acetaldehyde , lithium (medication) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , ethanol , endocrinology , medicine

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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