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用于乙烯基芳烃反马氏型碘代氧酰亚胺化反应的高价碘化合物。

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes.

作者信息

Krylov Igor B, Paveliev Stanislav A, Syroeshkin Mikhail A, Korlyukov Alexander A, Dorovatovskii Pavel V, Zubavichus Yan V, Nikishin Gennady I, Terent'ev Alexander O

机构信息

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation.

All-Russian Research Institute for Phytopathology, 143050 B. Vyazyomy, Moscow Region, Russian Federation.

出版信息

Beilstein J Org Chem. 2018 Aug 16;14:2146-2155. doi: 10.3762/bjoc.14.188. eCollection 2018.

DOI:10.3762/bjoc.14.188
PMID:30202467
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6122379/
Abstract

The iodo-oxyimidation of styrenes with the -hydroxyimide/I/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc) proved to be the most effective; yields of iodo-oxyimides are 34-91%. A plausible reaction pathway includes the addition of an imide--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.

摘要

有人提出了用α-羟基酰亚胺/碘/高价碘氧化剂体系对苯乙烯进行碘代氧酰亚胺化反应。在所研究的高价碘氧化剂（PIDA、PIFA、IBX、DMP）中，PhI(OAc)被证明是最有效的；碘代氧酰亚胺的产率为34-91%。一个合理的反应途径包括酰亚胺-α-氧基自由基加成到碳碳双键上，以及所得苄基自由基被碘捕获。结果表明，所制备的碘代氧酰亚胺中的碘原子可以被各种亲核试剂取代。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/87345195a69e/Beilstein_J_Org_Chem-14-2146-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/2d976863c22a/Beilstein_J_Org_Chem-14-2146-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/edd286b94796/Beilstein_J_Org_Chem-14-2146-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/00290f22126b/Beilstein_J_Org_Chem-14-2146-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/84af1ca14304/Beilstein_J_Org_Chem-14-2146-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/42fd4d9b77f2/Beilstein_J_Org_Chem-14-2146-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/d71c18a9fb0a/Beilstein_J_Org_Chem-14-2146-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/ae8126a540bc/Beilstein_J_Org_Chem-14-2146-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/87345195a69e/Beilstein_J_Org_Chem-14-2146-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/2d976863c22a/Beilstein_J_Org_Chem-14-2146-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/edd286b94796/Beilstein_J_Org_Chem-14-2146-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/00290f22126b/Beilstein_J_Org_Chem-14-2146-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/84af1ca14304/Beilstein_J_Org_Chem-14-2146-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/42fd4d9b77f2/Beilstein_J_Org_Chem-14-2146-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/d71c18a9fb0a/Beilstein_J_Org_Chem-14-2146-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/ae8126a540bc/Beilstein_J_Org_Chem-14-2146-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/77ca/6122379/87345195a69e/Beilstein_J_Org_Chem-14-2146-g009.jpg

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