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Rohde, Jan-Uwe
Transition Metal Chemistry
Research Interests
  • Inorganic chemistry, coordination chemistry, organometallic chemistry, chemical synthesis, catalysis, green chemistry, inorganic reaction mechanisms.

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Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation

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Title
Rapid access to polycyclic N-heteroarenes from unactivated, simple azines via a base-promoted Minisci-type annulation
Author
Lee, Jae BinKim, Gun HaJeon, Ji HwanJeong, Seo YeongLee, SoochanPark, JaehyunLee, DoyoungKwon, YoungkookSeo, Jeong KonChun, Joong-HyunKang, Seok JuChoe, WonyoungRohde, Jan-UweHong, Sung You
Issue Date
2022-05
Publisher
NATURE PORTFOLIO
Citation
NATURE COMMUNICATIONS, v.13, no.1, pp.2421
Abstract
Conventional synthetic methods to yield polycyclic heteroarenes have largely relied on metal-mediated arylation reactions requiring pre-functionalised substrates. However, the functionalisation of unactivated azines has been restricted because of their intrinsic low reactivity. Herein, we report a transition-metal-free, radical relay pi-extension approach to produce N-doped polycyclic aromatic compounds directly from simple azines and cyclic iodonium salts. Mechanistic and electron paramagnetic resonance studies provide evidence for the in situ generation of organic electron donors, while chemical trapping and electrochemical experiments implicate an iodanyl radical intermediate serving as a formal biaryl radical equivalent. This intermediate, formed by one-electron reduction of the cyclic iodonium salt, acts as the key intermediate driving the Minisci-type arylation reaction. The synthetic utility of this radical-based annulative pi-extension method is highlighted by the preparation of an N-doped heptacyclic nanographene fragment through fourfold C-H arylation. The functionalisation of unactivated azines has been restricted because of their intrinsic low reactivity. Here the authors show a transition-metal-free, radical relay pi-extension approach to produce N-doped polycyclic aromatic compounds directly from simple azines and cyclic iodonium salts.
URI
https://scholarworks.unist.ac.kr/handle/201301/58558
URL
https://www.nature.com/articles/s41467-022-30086-0
DOI
10.1038/s41467-022-30086-0
ISSN
2041-1723
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SE_Journal Papers
CHM_Journal Papers
ECHE_Journal Papers
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