Journal
CHEMICAL SCIENCE
Volume 2, Issue 11, Pages 2115-2119Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00357g
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Funding
- ACS Division of Organic Chemistry
- ACS PRF [49817-ND1]
- NIH [GM095666, RR08389-01]
- Sloan Foundation
- Beckman Foundation
- Research Corporation
- NSF [CHE-9208463, CHE-9629688]
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR008389] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM095666] Funding Source: NIH RePORTER
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Photocatalytic reactions of enones using metal polypyridyl complexes proceed by very different reaction manifolds in the presence of either Lewis or Bronsted acid additives. Previous work from our lab demonstrated that photocatalytic [2 + 2] cycloadditions of enones required the presence of a Lewis acidic co-catalyst, presumably to activate the enone and stabilize the key radical anion intermediate. On the other hand, Bronsted acid activators alter this reactivity and instead promote reductive cyclization reactions of a variety of aryl and aliphatic enones via a neutral radical intermediate. These two distinct reactive intermediates give rise to transformations differing in the connectivity, stereochemistry, and oxidation state of their products. In addition, this reductive coupling method introduces a novel approach to the tin-free generation of beta-ketoradicals that react with high diastereoselectivity and with the high functional group compatibility typical of radical cyclization reactions.
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