Abstract
The behavior of 2-naphthol and 7-bromo-2-naphthol as organic photoacids are exploited in organic synthesis for the preparation of benzyl sulfides (using a trichloroacetimidate derivative as the starting substrate) and polycyclic amines via acid catalyzed condensation of 1,2,3,4-tetrahydroisoquinoline with aldehydes.
Highlights
The behavior of 2-naphthol and 7-bromo-2-naphthol as organic photoacids are exploited tris(bipyridine)inruortghaennicisuynmth(eIsIis) fcohr tlhoerpidreeparation of benzyl sulfides and polycyclic amines via acid catalyzed condensation of 1,2,3,4tetrahydroisoquinoline with aldehydes
Photocatalysis emerged in the last decade as an established strategy for organic synthesis [1,2,3,4,5], in view of the v1e.rIsnatrtoidliutcytioonf the approach and the mild conditions adopted, including working at room temperature, the adPohpottoicoatnalyosfisaeqmueregoeduisn sthoellvasetndtescaadne das tahn esutabsleishoefdpsthraotetgoynfsoraosrgaantircascynetlheesssis r[1e–a5g], ent [6,7]
Direct HAT processes are currently limited to fewcatalysts, namely aromatic can be trapped kinetotnuersn[12b]yanadssuomiteabpolleyooxloemfienta,lalteeadderiinvagtivteos t(eh.ge.,fdoercmatuantgisotanteosafltas)n[1e3w]
Summary
Scheme S2c.hPermoep2o.sPerdopmosecdhmaencihsamnisfmorfothr ethaecaicdidinindducceeddfoformrmataiotnioonf souflfsiduelsfi3daensd3aalknadloiadlsk6aal,obidvisa 6a,b via photoexcited 2-napthol (* PA1). We demonstrated that molecules exhibiting a behavior as organophotoacids can be efficiently used in organic synthesis, in both C–S and C–C bond formation processes, avoiding the use of aggressive acids as well as of harsh conditions
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