A photo-driven traceless group directed electron–donor–acceptor (EDA) complex initiated radical coupling/dehydrogenation tandem reaction: access to 1-allyl/benzyl-3,4-dihydroisoquinoline

Abstract

A metal-free and mild one pot protocol for traceless group directed and electron-donor-acceptor (EDA) complex initiated radical coupling/dehydrogenation of arylazo-protected tetrahydroisoquinolines with benzyl/allyl halides is reported. The reaction was carried...

Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals

“…The method included the treatment of aryl azo-protected tetrahydroisoquinolines 11 a with the allyl or benzyl bromides 11 b in the presence of purple LED and a base to give corresponding substituted dihydro-isoquinolines 11 c in good yield (Scheme 11). [79] The method has a broad scope giving expedient access to an avenue of dihydro-isoquinolines. The screening suggested the importance of traceless directing azo-group as without it the reaction did not work.…”

Photoinduced Catalyst-Free Deuterodefunctionalization of Aryltriazenes with CDCl3

“…However, this method requires the use of expensive THF- d 8 or CD 3 OD as D sources and TFA- d 1 as a promoter (Scheme c) . Furthermore, based on our continual study on the development of safe and sustainable organic synthesis methodology with an easily available arylation reagent, − ,, we envisioned that aryltriazenes can be easily activated by light to produce aryl radicals and then abstract a deuterium atom from deuterated solvent. On the other hand, as far as we know, for previous methods of the synthesis of deuterated aromatic compounds mainly using CD 3 OD, CD 3 CN, THF- d 8 , DMF- d 7 , D 2 O, or D 2 , etc.…”