TY - JOUR
T1 - Metal-Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen-Containing Eight-Membered Ring System
AU - Kanyiva, Kyalo Stephen
AU - Marina, Tane
AU - Nishibe, Shun
AU - Shibata, Takanori
N1 - Funding Information:
This work was supported financially by a Grant‐in‐Aid for Scientific Research (C) (No. 18 K05114) from JSPS and Asahi Glass Research Proposal Grant (2019) for KSK. In this study, S.N. used the techniques of the GRRM program for DFT calculations supported by MANABIYA system of the Institute for Chemical Reaction Design and Discovery (ICReDD), Hokkaido University, which was established by World Premier International Research Initiative (WPI), MEXT, Japan. We also thank Dr. Natsuhiko Sugimura (Materials Characterization Central Laboratory, Waseda University) for his support to DFT calculations.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2021/6/8
Y1 - 2021/6/8
N2 - 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. (Figure presented.).
AB - 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. (Figure presented.).
KW - Alkynes; Dibenzazocines
KW - Aminoidodination
KW - Hypervalent Iodine
KW - Metal-Free Synthesis
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U2 - 10.1002/adsc.202100019
DO - 10.1002/adsc.202100019
M3 - Article
AN - SCOPUS:85103380961
SN - 1615-4150
VL - 363
SP - 2746
EP - 2751
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
IS - 11
ER -