Iodination of Isoquinoline by Trifluoromethanesulfonic Acid

Abstract

In this paper, we reported an unprecedented iodination of isoquinolines with high regioselectivity using N-Iodosuccinimide (NIS) to give 5-iodoisoquinoline. During the reaction, CF 3 SO 3 H is the key promoter to the success of this reaction. The methodology exhibited good yields and high functional group compatibility.

Unprecedented Direct Asymmetric Total Syntheses of 5,8’‐Naphthylisoquinoline Alkaloids from their Fully Substituted Precursors Employing a Novel Nickel/N,N‐ligand‐Catalyzed Atroposelective Cross‐Coupling Reaction

“…We were delighted to find that this compound could be transformed into the final building block 36 via an unprecedented, regioselective iodination procedure involving NIS in TfOH as the solvent of choice (Scheme 4). [24] …”

“…We were delighted to find that this compound could be transformed into the final building block 36 via an unprecedented, regioselective iodination procedure involving NIS in TfOH as the solvent of choice (Scheme 4). [24] Next, we decided to adapt Bringmann's previously described, highly efficient route towards the differently halogenated enantiomers S-45, S-46 and R-46 of the chiral dihydro isoquinoline building block. This approach featured a CuIcatalyzed Grignard addition to chiral Boc-protected aziridines Sand R-16, derived from commercially available d-or l-alaninol (S-and R-40) respectively.…”