5402-37-9Relevant academic research and scientific papers
Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes
Oakley, James V.,Stanley, Tyler J.,Jesse, Kate A.,Melanese, Amanda K.,Alvarez, Araceli A.,Prince, Aloha L.,Cain, Stephanie E.,Wenzel, Anna G.,Iafe, Robert G.
supporting information, p. 7063 - 7066 (2019/11/14)
A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to form 1,1-diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron-rich arene, employs readily available starting m
Gold-Catalyzed, SN1-Type Reaction of Alcohols to Afford Ethers and Cbz-Protected Amines
Vinson, Andrew R. S.,Davis, Victoria K.,Arunasalam, Arunamarie,Jesse, Kate A.,Hamilton, Rachael E.,Shattuck, Morgan A.,Hu, Allison C.,Iafe, Robert G.,Wenzel, Anna G.
supporting information, p. 765 - 770 (2015/03/30)
The use of a gold-catalyzed, microwave protocol to activate alcohols through an intermolecular, SN1-type reaction to directly form unsymmetrical ethers and N-benzyloxy carbamate- (Cbz) protected amines is reported. Results have shown this reaction to be highly reproducible and tolerant of moisture, and moderate to high product yields (53-99%) were obtained. Significantly, the intermolecular catalytic amination of alcohols to directly afford Cbz-protected amines is heretofore unprecedented using gold catalysis.
A Systematic Study of Benzyl Cation Initiated Cyclization Reactions
Angle, Steven R.,Louie, Michael S.
, p. 2853 - 2866 (2007/10/02)
A systematic investigation of benzyl cation inititiated cyclization reactions to form six-membered carbocycles is presented.The generation of benzyl cations from benzylic bromides, ethers, and alcohols followed by intramolecular capture provided good yields of cyclized products by use of several different cyclization terminators (e.g., phenyl, alkene, β-keto ester).A study on the effect of changing the electronic nature of substituents para to the benzyl cation showed that even electron-withdrawing substituents such as quaternary ammonium afford high yields of cyclization products.The formation of five- and seven-membered carbocycles was briefly investigated and found to be less general than the formation of the corresponding six-membered carbocycles.
