1322074-34-9Relevant academic research and scientific papers
Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts
Graskemper, Joseph W.,Wang, Bijia,Qin, Linlin,Neumann, Kiel D.,Dimagno, Stephen G.
scheme or table, p. 3158 - 3161 (2011/08/06)
For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.
Regiospecific reductive elimination from diaryliodonium salts
Wang, Bijia,Graskemper, Joseph W.,Qin, Linlin,DiMagno, Stephen G.
supporting information; experimental part, p. 4079 - 4083 (2010/08/07)
(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.
