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

Authors

  • Mark M. Maturi Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551, Japan
  • Ken Ohmori Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551, Japan
  • Keisuke Suzuki Department of Chemistry Tokyo Institute of Technology 2-12-1 O-okayama, Meguro-ku Tokyo 152-8551, Japan;, Email: ksuzuki@chem.titech.ac.jp

DOI:

https://doi.org/10.2533/chimia.2018.870

PMID:

30648953

Keywords:

Aryne, Benzaldehydes, Benzocyclobutenols, Cycloaddition, Ring opening

Abstract

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.
CHIMIA Vol. 72 No. 12(2018): Chemistry Ties Linking Japan to Switerland

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Published

2018-12-19

Issue

Vol. 72 No. 12 (2018): Chemistry Ties Linking Japan to Switerland

Section

Scientific Articles

License

Copyright (c) 2018 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
M. M. Maturi, K. Ohmori, K. Suzuki, Chimia 2018, 72, 870, DOI: 10.2533/chimia.2018.870.