Boron‐Catalyzed C−C Functionalization of Allyl Alcohols

Boron‐Catalyzed C−C Functionalization of Allyl Alcohols

Tris(pentafluorophenyl)borane‐catalyzed C−C bond functionalization of arylallyl alcohols using donor‐acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-03, Vol.361 (6), p.1301-1306
Hauptverfasser: Rao, Santhosh, Kapanaiah, Raja, Prabhu, Kandikere Ramaiah
Format: Artikel
Sprache:eng
Schlagworte:
Alcohol
Alcohols
allyl alcohol
Boron
carbene
Carbenes
Carbon
Cleavage
C−C functionalization
diazo
Homology
Hydroxyl groups
tris(pentafluorophenyl)borane
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Zusammenfassung:Tris(pentafluorophenyl)borane‐catalyzed C−C bond functionalization of arylallyl alcohols using donor‐acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal‐free transformation presents a novel disconnection strategy towards carbon‐carbon bond scission and formation.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801389