Oxidative Fluoroarylation of Benzylidenecyclopropanes with HF·Py and Aryl Iodides via Iodonio-[3,3]-Rearrangement

Reported herein is an in situ-generated hypervalent iodine-incorporating fluoroarylation of benzylidenecyclopropanes using commercially available HF·Py and aryl iodides as fluorine and aryl sources, respectively. The reaction proceeds via regioselective 1,2-fluoroiodination of a double bond followed...

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Published inOrganic letters Vol. 24; no. 18; pp. 3389 - 3394
Main Authors Huang, Long-Ling, Lin, Peng-Peng, Li, Yu-Xin, Feng, Si-Xin, Tu, Fang-Hai, Yang, Shuang, Zhao, Gui-Yang, Huang, Zhi-Shu, Wang, Honggen, Li, Qingjiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.05.2022
Amer Chemical Soc
Subjects
Alkenes - chemistry
Chemistry
Chemistry, Organic
Iodides
Iodine - chemistry
Oxidation-Reduction
Oxidative Stress
Physical Sciences
Science & Technology
ALKENES
IODONIO-CLAISEN REARRANGEMENT
FLUORINATION
AMINOFLUORINATION
CONSTRUCTION
DIFLUORINATION
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Summary:Reported herein is an in situ-generated hypervalent iodine-incorporating fluoroarylation of benzylidenecyclopropanes using commercially available HF·Py and aryl iodides as fluorine and aryl sources, respectively. The reaction proceeds via regioselective 1,2-fluoroiodination of a double bond followed by an iodonio-[3,3]-rearrangement of the formed cyclopropyl-I(III) species. The protocol offers facile access to valuable monofluorinated 1,1-bis-benzyl-alkenes with mild reaction conditions and moderate to good yields. The synthetic utility of the products was demonstrated by further transformations. Preliminary mechanistic studies were conducted.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01150