Lactonization with concomitant 1,2-aryl migration and alkoxylation mediated by dialkoxyphenyl iodides generated in situ

A series of alkoxylated isobenzofuranones were conveniently synthesized from the reaction of 2-(1-arylvinyl)benzoic acids with PhI(OR) 2 , generated in situ from the reaction of iodosobenzene (PhIO) with alkyl alcohols. This hypervalent iodine mediated one-pot transformation is postulated to undergo...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-07, Vol.57 (60), p.7426-7429
Main Authors: Zhang, Jingran, Jalil, Ayesha, He, Jiaxin, Yu, Zhenyang, Cheng, Yifu, Li, Guangchen, Du, Yunfei, Zhao, Kang
Format: Article
Language:English
Subjects:
Alcohols
Aromatic compounds
Benzoic acid
Cascade chemical reactions
Chemical reactions
Chemical synthesis
Crystallography
Iodides
Iodine
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Summary:A series of alkoxylated isobenzofuranones were conveniently synthesized from the reaction of 2-(1-arylvinyl)benzoic acids with PhI(OR) 2 , generated in situ from the reaction of iodosobenzene (PhIO) with alkyl alcohols. This hypervalent iodine mediated one-pot transformation is postulated to undergo a cascade reaction involving lactonization, 1,2-aryl migration and alkoxylation processes. The organocatalytic and chiral organoiodine-catalyzed asymmetric reactions of the current transformation were also probed.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03110d