2021
DOI: 10.1002/adsc.202100019
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Metal‐Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen‐Containing Eight‐Membered Ring System

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 c… Show more

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Cited by 9 publications
(3 citation statements)
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“…Consequently, the coupling of an iodine radical and B affords an 8-membered heterocycle ( 66 ) (Scheme 42). 100…”
Section: Synthesis and Functionalisation Of Heterocycles Using Hyperv...mentioning
confidence: 99%
See 1 more Smart Citation
“…Consequently, the coupling of an iodine radical and B affords an 8-membered heterocycle ( 66 ) (Scheme 42). 100…”
Section: Synthesis and Functionalisation Of Heterocycles Using Hyperv...mentioning
confidence: 99%
“…Consequently, the coupling of an iodine radical and B affords an 8-membered heterocycle (66) (Scheme 42). 100 A visible-light-induced synthesis of oxindoles via a one-pot tandem reaction of N-arylacrylamides (67), difluoroacetic acid and PhI(OAc) 2 was established by the He group. The protocol avoids the use of additives, base, metal-catalysts, and external photosensitisers.…”
Section: Organic and Biomolecular Chemistry Reviewmentioning
confidence: 99%
“…Kanyiva, Shibata, and co-workers detailed a cost-effective method to access the iodinated dihydrodibenzo[ c , e ]azocine derivatives through visible light-induced intramolecular regioselective aminoiodination reaction, during which various substituted alkynes were easily furnished without using metal catalysts (Scheme 32). 61 Notably, the products could be modified under simple conditions. 99a would easily achieve the departure of p -toluenesulfonyl and iodine atom and the reduction of alkene groups in one pot.…”
Section: Visible Light-induced Systemmentioning
confidence: 99%