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Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile‐tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)‐catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N‐propargyl carboxamides and arenes, representing first C(sp3)−C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo‐dig modes. [ABSTRACT FROM AUTHOR]

As a first example of metal-free and catalytic fluorinative transformations of alkynes, we developed a cycloisomerization-fluorination sequence of N-propargyl amides catalyzed by an iodine(III) species. The iodine(III) catalyst is in situ generated from iodoarene as a precatalyst with Selectfluor as a fluorinating oxidant in the presence of HF⋅pyridine. [ABSTRACT FROM AUTHOR]

A hypervalent iodine(III) catalyst, generated in situ from these reagents, is effective on the dehydrogenative cycloisomerization/arylation reaction of I N i -propargyl carboxamides and arenes. Keywords: arylation; catalysis; cyclization; iodine; metal-free EN arylation catalysis cyclization iodine metal-free 1913 1913 1 06/23/22 20220621 NES 220621 The front cover picture illustrates iodoarene as a precatalyst and dimethyl(fluoro)- SP 6 sp -sulfane as a real oxidant derived from DMSO and F-TEDA-PF SB 6 sb , and the Japanese kanji stands for the initial letters of key elements, sulfur, iodine, and fluorine. Front Cover Picture: Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis (Adv. [Extracted from the article]

The combination of cyclization and fluorination in a single operation provides a straightforward and efficiENt approach to fluorinated heterocycles from unsaturated compounds bearing a heteroatom nucleophile. In this study, a metal ‐ free cycloisomerization–fluorination sequENce of N ‐ propargyl amides catalyzed by an iodine(III) species is reported. The iodine(III) catalyst is in situ gENerated from iodoarENe as a precatalyst with Selectfluor as a fluorinating oxidant in the presENce of HF⋅pyridine. More information can be found in the Communication by Akio Saito et   al. on page   1314 in Issue 11, 2016 (DOI: 10.1002/ajoc.201600383). [ABSTRACT FROM AUTHOR]