Visible-Light-Enabled Paternò–Büchi Reaction via Triplet Energy Transfer for the Synthesis of Oxetanes
| Autor: | Corinna S. Schindler, Katie A. Rykaczewski |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Cycloaddition Reaction
Light Molecular Structure Photochemistry Ultraviolet Rays Chemistry Aryl Organic Chemistry chemistry.chemical_element Stereoisomerism Alkenes Biochemistry Paternò–Büchi reaction Cycloaddition Benzophenones chemistry.chemical_compound Energy Transfer Ethers Cyclic Yield (chemistry) Glyoxylates Photocatalysis Iridium Physical and Theoretical Chemistry Visible spectrum |
| Zdroj: | Organic Letters. 22:6516-6519 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | One of the most efficient ways to synthesize oxetanes is the light-enabled [2 + 2] cycloaddition reaction of carbonyls and alkenes, referred to as the Paternò-Büchi reaction. The reaction conditions for this transformation typically require the use of high energy UV light to excite the carbonyl, limiting the applications, safety, and scalability. We herein report the development of a visible-light-mediated Paternò-Büchi reaction protocol that relies on triplet energy transfer from an iridium-based photocatalyst to the carbonyl substrates. This mode of activation is demonstrated for a variety of aryl glyoxylates and negates the need for both visible-light-absorbing carbonyl starting materials and UV light to enable access to a variety of functionalized oxetanes in up to 99% yield. |
| Databáze: | OpenAIRE |
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