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Overriding Norrish Type II to Access Cyclopropanols.

James W Pearson1, Samantha L Dudra1, Anthony F Palermo1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.

Journal of the American Chemical Society
|September 30, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new photocyclization method for creating cyclopropanols from aryl ketones. This breakthrough overcomes limitations in synthesizing small, medicinally important ring systems using photochemistry.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • The Norrish-Yang photocyclization is a key method for synthesizing cyclobutanols.
  • Accessing smaller ring systems like cyclopropanols via photocyclization is challenging due to kinetic preferences.
  • 1,5-hydrogen atom transfer (HAT) typically dominates over 1,4-HAT in photoexcited aryl ketones.

Purpose of the Study:

  • To develop a novel photocyclization strategy for synthesizing cyclopropanols.
  • To overcome the kinetic preference for 1,5-HAT in favor of 1,4-transfer.
  • To establish a mild and versatile method for accessing valuable cyclopropanol scaffolds.

Main Methods:

  • Utilized β-boryl aryl ketones as substrates.
  • Employed solvent-controlled selective population of triplet states (π,π* over n,π*).
  • Investigated the mechanism of 1,4-boryl group transfer versus 1,5-HAT.

Main Results:

  • Demonstrated the first successful photocyclization of β-boryl aryl ketones to cyclopropanols.
  • Achieved selective 1,4-boryl group transfer, bypassing the favored 1,5-HAT.
  • The reaction proceeds under mild conditions with broad functional group tolerance.

Conclusions:

  • This work presents a novel and efficient route to cyclopropanols via photocyclization.
  • The developed method provides access to medicinally relevant 3-membered rings previously difficult to synthesize.
  • The strategy offers a versatile platform for generating diverse cyclopropanol derivatives.