209863-08-1Relevant academic research and scientific papers
Novel chiral bis-phosphoramides as organocatalysts for tetrachlorosilane-mediated reactions
Rossi, Sergio,Ziliani, Marco,Annunziata, Rita,Benaglia, Maurizio
supporting information, (2018/01/12)
The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/pri
Catalytic oxidative cyclization of 2′-arylbenzaldehyde oxime ethers under photoinduced electron transfer conditions
Hofstra, Julie L.,Grassbaugh, Brittany R.,Tran, Quan M.,Armada, Nicholas R.,De Lijser, H. J. Peter
, p. 256 - 265 (2016/09/09)
A series of 2′-arylbenzaldehyde oxime ethers were synthesized and shown to generate the corresponding phenanthridines upon irradiation in the presence of 9,10-dicyanoanthracene in acetonitrile. Mechanistic studies suggest that the oxidative cyclization reaction sequence is initiated by an electron transfer step followed by nucleophilic attack of the aryl ring onto the nitrogen of the oxime ether. A concave downward Hammett plot is presumably the result of a change in charge distribution in the radical cation species with strongly electron-donating substituents that yields a less electrophilic nitrogen atom and a decreased amount of cyclized product. The reaction is selective (no nitrile byproduct is formed unlike other photochemical reactions involving aldoxime ethers) as well as regiospecific when using 2′-aryl groups with metasubstituents, making this reaction a useful alternative for preparing substituted phenanthridines.
The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes
Chamoin,Houldsworth,Kruse,Bakker, W. Iwema,Snieckus
, p. 4179 - 4182 (2007/10/03)
The synthesis of the titled compounds by Suzuki-Miyaura cross coupling on Merrifield resin - Leznoff acetal - linked halo benzaldehydes followed by mild acid hydrolysis is reported; synthetic utility for heterocycles based on solution phase Directed ortho Metalation chemistry is demonstrated.
