Journal
ORGANIC LETTERS
Volume 18, Issue 20, Pages 5444-5446Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02727
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Funding
- JSPS [26248031]
- Scientific Research on Innovative Areas 2707 Middle Molecular Strategy from MEXT [15H05850]
- Grants-in-Aid for Scientific Research [26248031, 15K13699, 15H05850] Funding Source: KAKEN
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A Cossy 5-exo-dig photocyclization of organo-halides (X = Br, I) onto a C-C triple bond was studied using a flow photomicroreactor, which proceeded in a minute order of residence time. A deuterium labeling study supported the nonchain radical mechanism proposed by the Cossy group, in which a hydrogen source originates from a triethylamine cation radical. Scalable flow synthesis using a larger volume of flow reactor was also successful, providing 4 g of the product in high yield.
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