727401-27-6Relevant articles and documents
Graphene oxide catalyzed ketone α-alkylation with alkenes: Enhancement of graphene oxide activity by hydrogen bonding
Meng, Guangrong,Patel, Mehulkumar,Luo, Feixiang,Li, Qingdong,Flach, Carol,Mendelsohn, Richard,Garfunkel, Eric,He, Huixin,Szostak, Michal
supporting information, p. 5379 - 5382 (2019/05/10)
Direct α-alkylation of carbonyl compounds represents a fundamental bond forming transformation in organic synthesis. We report the first ketone-alkylation using olefins and alcohols as simple alkylating agents catalyzed by graphene oxide. Extensive studies of the graphene surface suggest a pathway involving dual activation of both coupling partners. Notably, we show that polar functional groups have a stabilizing effect on the GO surface, which results in a net enhancement of the catalytic activity. The method represents the first alkylation of carbonyl compounds using graphenes, which opens the door for the development of an array of protocols for ketone functionalization employing common carbonyl building blocks and readily available graphenes.
Solvent-free alkylation of 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols catalyzed by La(NO3)3·6H2O
Subramanyam, Madala,Rao, Koya Prabhakara,Varala, Ravi,Rao, Mandava V. Basaveswara
, p. 1155 - 1160 (2016/03/01)
An efficient and solvent free method for benzylation, propargylation and allylation of 1,3-dicarbonyl compounds with alcohols has been developed by using La(NO3)3·6H2O as water tolerable catalyst. The reaction was shown to proceed smoothly for various 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols including 1° allylic alcohols, without any solvent, providing a clean access to the desired products in short reaction times with good to excellent yields and high selectivity.
Ruthenium salophen triflate: A reusable catalyst for alkylation of 1,3-dicarbonyl compounds
Barati, Behjat,Moghadam, Majid,Rahmati, Abbas,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj
, p. 122 - 126 (2013/01/15)
Reaction of 1,3-dicarbonyl compounds with alcohols or olefins in the presence of catalytic amounts of electron-deficient [Ru(salophen)OTf] produced α-alkylated 1,3-dicarbonyls under solvent-free conditions. Different substituted benzylic alcohols were efficiently reacted with 2,4-pentanedione or 1,3-diphenyl-1,3-propanedione and their corresponding alkylated diones were obtained in good to excellent yield. On the other hand, substituted styrenes were also converted to their corresponding α-alkylated 1,3-dicarbonyls in good yields. The effect of reaction parameters such as solvent, amount of catalyst and axial substituent on the ruthenium salophen was also investigated. The catalyst was reusable several times without loss of its activity.
