136019-61-9Relevant academic research and scientific papers
On the Route to the Photogeneration of Heteroaryl Cations. the Case of Halothiophenes
Raviola, Carlotta,Chiesa, Francesco,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
, p. 6336 - 6342 (2016)
2-Chloro-, 2-bromo-, and 2-iodothiophenes undergo photochemical dehalogenation via the triplet state. In the presence of suitable π-bond nucleophiles, thienylation occurs with modest yield from chloro and bromo derivatives (via photogenerated triplet 2-thienyl cation). Specific trapping by using oxygen along with computational analysis carried out by means of a density functional method support that, in the case of iodo derivatives, homolytic thienyl-I bond fragmentation occurs first and heteroaryl cations are formed by electron transfer within the triplet radical pair, thus opening an indirect access to such cations.
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.
