- On the Route to the Photogeneration of Heteroaryl Cations. the Case of Halothiophenes
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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.
- Raviola, Carlotta,Chiesa, Francesco,Protti, Stefano,Albini, Angelo,Fagnoni, Maurizio
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p. 6336 - 6342
(2016/08/16)
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- REACTION OF ALLYLTRIMETHYLSILANE WITH AN AROMATIC COMPOUND USING HYPERVALENT ORGANOIODINE COMPOUND: A NEW ALLYLATION OF AROMATIC COMPOUNDS
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New general method for the allylation of aromatic compounds from allyltrimethylsilane utilizing the combination of iodosylbenzene and BF3 OEt2 are described, which is based upon the umpolung of allyltrimethylsilane by way of cationic allylphenyliodonium (III) salt complex as an intermediate.
- Lee, Kilsung,Kim, Dae Young,Oh, Dong Young
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p. 667 - 668
(2007/10/02)
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