4.8 Article

Crossed Intermolecular [2+2] Cycloadditions of Acyclic Enones via Visible Light Photocatalysis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 41, Pages 14604-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja903732v

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Funding

  1. Beckman Foundation and the Research Corporation
  2. NSF [CHE-9208463, CHE9629688]
  3. NIH [RR08389-01]

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Efficient [2+2] heterodimerizations of dissimilar acyclic enones can be accomplished upon visible light irradiation in the presence of a ruthenium(II) photocatalyst. Similar cycloadditions under standard UV photolysis conditions are inefficient and unselective. Nevertheless, a diverse range of unsymmetrical tri- and tetrasubstituted cyclobutane structures can be produced in good yields and excellent diastereoselectivities using this new method. The reaction is promoted by any visible light source, and efficient, gram-scale cycloadditions can be conducted upon irradiating with ambient sunlight.

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