The cyclization of N-alkenylamides catalyzed by iodoarenes under oxidative conditions is presented. Five-, six-, and seven-membered rings with a range of substitutions can be prepared by this route. Preliminary data from the use of chiral iodoarenes as precatalysts show that enantiocontrol is feasible.

The oxidation of iodoarenes is central to the field of hypervalent iodine chemistry. It was found that the metathetical redox reaction between (diacetoxyiodo)arenes and iodoarenes is possible in the presence of a catalytic amount of Lewis acid. This discovery opens a new strategy to access (diacetoxyiodo)arenes. A computational study is provided to rationalize the results observed.

Neutral organic electron donors, featuring pyridinylidene-imidazolylidene, pyridinylidene-benzimidazolylidene and imidazolylidene-benzimidazolylidene linkages are reported. The pyridinylidene-benzimidazolylidene and imidazolylidene-benzimidazolylidene hybrid systems were designed to be the first super electron donors to convert iodoarenes to aryl radicals at room temperature, and indeed both sh...

The development of new methodologies to affect non-ortho-functionalization of arenes has emerged as a globally important arena for research, which is key to both fundamental studies and applied technologies. A range of simple arene feedstocks (namely, biphenyl, meta-terphenyl, para-terphenyl, 1,3,5-triphenylbenzene, and biphenylene) is transformed to hitherto unobtainable multi-iodoarenes via a...

Nanoporous metallic glass Pd, which was fabricated by dealloying of a glassy metallic alloy Pd(30)Ni(50)P(20), exhibited a remarkable catalytic activity for the Suzuki-coupling reaction between iodoarenes and arylboronic acids under mild conditions. Moreover, the catalyst can be reused several times without a significant loss of catalytic activity.

Enantiopure C2-symmetric iodoarenes based on the rigid all-carbon anti-dimethanoanthracene framework are shown to catalyse the asymmetric oxidative Kita spirolactonisation of propanoic acid-tethered 1-naphthols with significant levels of asymmetric induction of up to 67% ee.

An unprecedented silver-catalyzed formal insertion of arynes into Rf-I (Rf = CF3, C2F5) bonds has been developed. This protocol provides easy access to various ortho-perfluoroalkyl iodoarenes under mild conditions. In this insertion reaction, an ionic atom-transfer reaction of RfI occurs, and a silver-mediated metathesis process is involved in the efficient transfer of the electropositive iodin...

Cu(I)-diamine complexes were found to catalyse the trifluoromethylation of aryl iodides. In the presence of a small amount of CuX (X = Cl, Br, I) and 1,10-phenanthroline (phen), the cross-coupling reactions of iodoarenes with trifluoromethylsilanes proceeded smoothly to afford trifluoromethylated aromatics in good yields.

Tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3] catalyzed asymmetric double carbohydroamination of iodoarenes in the presence of a chiral ligand (Trost ligand and Me-DuPHOS are most effective) is an excellent method for the chiral synthesis of alpha-aminoamides in up to 99% ee.

Cu- and Pd-catalyzed arylation of aminocholanes has been described for the first time. While this Cu-catalyzed protocol provides high yields in reactions of aminocholanes with iodoarenes, Pd catalysis was found to be preferable for the reactions of aminocholanes with dichloroanthraquinones. UV-vis titration of bis(cholanylamino)anthraquinones with a series of cations demonstrated their high bin...