Radical Cations

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� “Cation pool” oxidizes benzylsilane directly BF 4 – N CO 2Me Me 3Si π-C-X •+ Bond Dissociation OMe DCM, –50 °C � Oxidation potential of benzylsilane must be
Me 3Si � Stronger oxidant than iminium ion N CO 2Me OMe N CO 2Me Proposed Mechanism OMe Me 3Si Me 3Si Propagation Propagation OMe BF 4 – N CO 2Me OMe OMe Initiation BF 4 – N CO 2Me OMe Me 3Si + N CO 2Me J. Yoshida et al. J. Am. Chem. Soc. 2007, 129, 1902.
Page 1 and 2: Radical Cations •+ : Generation,
Page 3 and 4: � Stoichiometric oxidant: SET Bn
Page 5 and 6: � Anodic oxidation MeO N H N CO 2
Page 7 and 8: Primary Fate of Radical Cations Sym
Page 9 and 10: Thermochemical Cycle: Calculating p
Page 11 and 12: Me Ph Ph O Ph O Ph O Deprotonation
Page 13 and 14: π-RH •+ Deprotonation � π-RH
Page 15 and 16: n-RH •+ Deprotonation � n-RH
Page 17 and 18: σ-CH •+ Deprotonation � Deprot
Page 19 and 20: π-AH •+ Deprotonation � π-OH
Page 21 and 22: � Reaction at the ortho-position
Page 25 and 26: π-A-B •+ Bond Dissociation � C
Page 27 and 28: � Limited mostly to azoalkanes an
Page 29 and 30: π-C-C •+ Bond Dissociation � F
Page 31 and 32: π-C-C •+ Bond Dissociation � N
Page 33 and 34: n-C-C •+ Bond Dissociation � To
Page 35 and 36: Me 3SiO σ-C-C •+ Bond Dissociati
Page 37 and 38: π-C-X •+ Bond Dissociation: Calc
Page 39 and 40: π-C-X •+ Bond Dissociation � R
Page 41: � “Cation pool” oxidizes benz
Page 45 and 46: ClO 4 - N Me NC Ph CN σ-C-X •+ B
Page 47 and 48: � Moeller en route to (-)-alliaco
Page 49 and 50: N PTOC PTOC = Nu-n-A-B •+ AcOH N
Page 53 and 54: Diels-Alder [4 + 2] Cycloaddition
Page 55 and 56: � Photoredox catalyzed radical ca
Page 59 and 60: Primary Fate of Radical Cations �
Page 61 and 62: � The Hofmann-Löffler-Freytag re
Page 63 and 64: � Epoxonium cyclization Bn O OMe
Page 65: H H H O R !-arylation O intramolecu

Radical Cations

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