Radical-mediated anti-markovnikov hydrophosphonation of olefins

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6429-6431

  Daeffler, Christopher S ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84055224005     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202790n     Document Type: Article

References (26)

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23. Additionally, standard radical conditions produce the P(O)- Ph3-BF3 adduct as a side product that is difficult to separate from the crude reaction mixture.
24. [HPPh3][PF6] and [HPPh3][Br] are not effective as hydrophosphonating reagents under photochemical conditions. Further experiments showed that the reaction would not continue without irradiation.
25. All reactions were carried out in Pyrex glassware with a watercooled, quartz-jacketedUVlamp. See Supporting Information for more details.
26. Crude 1[BF4] was obtained from photochemical hydrophosphonation conditions, where the mixture contains unreacted 4-allylanisole, [HPPh3][BF4], and PPh3.