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Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF<sub>2</sub>H‐Containing Alcohols
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- Yusuke Arai
- Chemical Resources Laboratory Tokyo Institute of Technology R1-27, 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Ren Tomita
- Chemical Resources Laboratory Tokyo Institute of Technology R1-27, 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Gaku Ando
- Chemical Resources Laboratory Tokyo Institute of Technology R1-27, 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Takashi Koike
- Chemical Resources Laboratory Tokyo Institute of Technology R1-27, 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Munetaka Akita
- Chemical Resources Laboratory Tokyo Institute of Technology R1-27, 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF<jats:sub>2</jats:sub>H) group into alkenes by visible‐light‐driven photoredox catalysis. The use of <jats:italic>fac</jats:italic>‐[Ir(ppy)<jats:sub>3</jats:sub>] (ppy=2‐pyridylphenyl) photocatalyst and shelf‐stable Hu's reagent, <jats:italic>N</jats:italic>‐tosyl‐<jats:italic>S</jats:italic>‐difluoromethyl‐<jats:italic>S</jats:italic>‐phenylsulfoximine, as a CF<jats:sub>2</jats:sub>H source is the key to success. The well‐designed photoredox system achieves synthesis of not only β‐CF<jats:sub>2</jats:sub>H‐substituted alcohols but also ethers and an ester from alkenes through solvolytic processes. The present method allows a single‐step and regioselective formation of C(sp<jats:sup>3</jats:sup>)–CF<jats:sub>2</jats:sub>H and C(sp<jats:sup>3</jats:sup>)−O bonds from C=C moiety in alkenes, such as hydroxydifluoromethylation, regardless of terminal or internal alkenes. Moreover, this methodology tolerates a variety of functional groups.</jats:p>
Journal
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- Chemistry – A European Journal
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Chemistry – A European Journal 22 (4), 1262-1265, 2015-12-16
Wiley
