Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF 2 H‐Containing Alcohols
Abstract We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF 2 H) group into alkenes by visible‐light‐driven photoredox catalysis. The use of fac ‐[Ir(ppy) 3 ] (ppy=2‐pyridylphenyl) photocatalyst and shelf‐stable Hu's reagent, N ‐tosyl‐ S ‐difluoro...
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| Published in | Chemistry : a European journal Vol. 22; no. 4; pp. 1262 - 1265 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
22.01.2016
|
| Online Access | Get full text |
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| Summary: | Abstract
We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF
2
H) group into alkenes by visible‐light‐driven photoredox catalysis. The use of
fac
‐[Ir(ppy)
3
] (ppy=2‐pyridylphenyl) photocatalyst and shelf‐stable Hu's reagent,
N
‐tosyl‐
S
‐difluoromethyl‐
S
‐phenylsulfoximine, as a CF
2
H source is the key to success. The well‐designed photoredox system achieves synthesis of not only β‐CF
2
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
3
)–CF
2
H and C(sp
3
)−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. |
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| ISSN: | 0947-6539 1521-3765 |
| DOI: | 10.1002/chem.201504838 |