Issue 60, 2021
From the journal:

Chemical Communications

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

Jingran Zhang,‡a   Ayesha Jalil,‡a   Jiaxin He,a   Zhenyang Yu,a   Yifu Cheng,a   Guangchen Li,a   Yunfei Du ORCID logo *a  and  Kang Zhao*b  

* Corresponding authors

a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
E-mail: duyunfeier@tju.edu.cn

b State Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, China
E-mail: zhaokang@sdu.edu.cn

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/D1CC03110D
Article type
Communication
Submitted
12 Jun 2021
Accepted
28 Jun 2021
First published
29 Jun 2021

Chem. Commun., 2021,57, 7426-7429

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

J. Zhang, A. Jalil, J. He, Z. Yu, Y. Cheng, G. Li, Y. Du and K. Zhao, Chem. Commun., 2021, 57, 7426 DOI: 10.1039/D1CC03110D

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