4.7 Article

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 26, Pages 3271-3274

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc00621e

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Funding

  1. National Natural Science Foundation of China [21762025, 21562026]
  2. Key Projects of Natural Science Foundation of Jiangxi Province [20192ACBL200 26]

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The research achieved direct formylation of benzothiazo/les and isoquinolines through a novel iron-catalyzed Minisci-type oxidative coupling process, with exceedingly mild reaction conditions and broad functional group tolerance.
The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

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