Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 34, Pages 8991-8994Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405359
Keywords
cycloadditions; energy transfer; photochemistry; small ring systems; total synthesis
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Funding
- National Institutes of Health [GM095666]
- NSF [CHE-1048642]
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[2+2] Photocycloadditions of 1,3-dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3-dienes. The ability to use long-wavelength visible light is attractive because these reaction conditions tolerate the presence of sensitive functional groups that might be readily decomposed by the high-energy UVC radiation required for direct photo-excitation of 1,3-dienes. The resulting vinylcyclobutane products are poised for a variety of further diversification reactions, and this method is consequently expected to be powerfully enabling in the synthesis of complex organic targets.
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