Hypervalent Iodine Compounds for anti-Markovnikov-type Iodo-Oxyimidation of Vinylarenes Full article
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Beilstein Journal of Organic Chemistry
ISSN: 1860-5397 |
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Output data | Year: 2018, Volume: 14, Pages: 2146-2155 Pages count : 10 DOI: 10.3762/bjoc.14.188 | ||||||||||
Tags | free radicals; hypervalent iodine; imide-N-oxyl radicals; iodination; N-hydroxyimides; oxidative functionalization | ||||||||||
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Abstract:
The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.
Cite:
Krylov I.B.
, Paveliev S.A.
, Syroeshkin M.A.
, Korlyukov A.A.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Nikishin G.I.
, Terent’ev A.O.
Hypervalent Iodine Compounds for anti-Markovnikov-type Iodo-Oxyimidation of Vinylarenes
Beilstein Journal of Organic Chemistry. 2018. V.14. P.2146-2155. DOI: 10.3762/bjoc.14.188 WOS Scopus РИНЦ
Hypervalent Iodine Compounds for anti-Markovnikov-type Iodo-Oxyimidation of Vinylarenes
Beilstein Journal of Organic Chemistry. 2018. V.14. P.2146-2155. DOI: 10.3762/bjoc.14.188 WOS Scopus РИНЦ
Files:
Full text from publisher
Dates:
Submitted: | May 27, 2018 |
Accepted: | Jul 31, 2018 |
Published online: | Aug 16, 2018 |
Identifiers:
Web of science | WOS:000441824800001 |
Scopus | 2-s2.0-85052236684 |
Elibrary | 35783809 |
Chemical Abstracts | 2018:2026457 |
OpenAlex | W2886173172 |