Nickel(II)‐Mediated Regioselective CH Monoiodination of Arenes and Heteroarenes by using Molecular Iodine

Abstract

The8 -aminoquinoline-directed, nickel(II)-mediated ortho-iodination of benzamides using molecular iodine has been developed. The process is highly regioselective and furnishes only monoiodinated products. Ab road range of arenes and heteroarenes with diverse functional groups provided monoiodinated productsi ng ood to excellent yields.

Metal–free C5‐H Bromination of Quinolines for One‐pot C−X (X=C, O, S) Bond Formations

“…The result is in sharp contrast with that of our thiolation system in which only a mixture of thiolated products (on benzamides or quinoline motif) can be obtained . Herein, the bromination of quinoline ring is favored over the metalation–deprotonation (CMD) process at the ortho ‐position of benzamide . Furthermore, arylated product in moderate yield can be obtained in the two cases of heterocyclic amides ( 5 h and 5 i ).…”

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

“…[154][155][156][157][158][159] TheR h III -catalyzed C À Hb romination or iodination of benzamides with N-bromosuccinimide (NBS) or Niodosuccinimide (NIS), respectively was reported by Glorius and co-workers (Scheme 47 a). Major progress in CÀHh alogenation was achieved by using various electrophilic halogenating reagents,although in afew cases ad ihalogen (e.g.I 2 )w as used as the halogen source.…”

The mechanism of directed Ni(ii)-catalyzed C–H iodination with molecular iodine

“…The design of the first-row transition metal catalysts for this reaction is expected to be even more challenging because of the amphiphilic or “chameleon” nature of the I 2 molecule, which can act as either an electron-donor (L-type) or electron-acceptor (Z-type) ligand in transition metal complexes. 56 – 58 As a major advancement in this field, the Ni( ii )-catalyzed C–H iodination of an AQ substrate with I 2 with N , N ′-directing groups was recently reported by both Chatani and coworkers 59 and Koley and coworkers 60 ( Fig. 1 ).…”