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Metal‐Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen‐Containing Eight‐Membered Ring System
Author(s) -
Kanyiva Kyalo Stephen,
Marina Tane,
Nishibe Shun,
Shibata Takanori
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100019
Subject(s) - chemistry , intramolecular force , hypervalent molecule , alkyne , regioselectivity , iodine , ring (chemistry) , photochemistry , visible spectrum , irradiation , polymer chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , physics , optoelectronics , nuclear physics
Abstract A method for the synthesis of dihydrodibenzo[ c , e ]azocine derivatives via a regioselective intramolecular aminoiodination of alkynes under visible light irradiation has been developed. This protocol uses a combination of iodine and hypervalent iodine to realize a sulfonamidyl radical, followed by intramolecular addition to alkyne to form a vinyl radical. Subsequent trapping of iodine radical affords an 8‐membered heterocycle. Applications of the obtained iodinated 8‐membered heterocycles in the Suzuki‐Miyaura coupling and deiodination are also demonstrated.