Tandem Vinylogous Aldol and Intramolecular [2 + 2] Cycloaddition toward Benzocyclobutenes by UV Light Photocatalysis

A facile and efficient radical tandem vinylogous aldol and intramolecular [2 + 2] cycloaddition reaction for direct synthesis of cyclobutane-containing benzocyclobutenes (BCBs) under extremely mild conditions without using any photocatalysts is reported. This approach exhibited definite compatibilit...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (15), p.3304-3309
Main Authors: Tan, Hong-bo, Liu, Ying-shan, Zhou, Jia-ying, Cao, Man, Lei, Tong, Ren, Si-ying, Lin, Chang-qiu, Yang, Yi-fan, Hu, Zhang-liang, Xu, Zhi-gang, Tang, Dian-yong, Chen, Zhong-zhu, Qu, Xian-you
Format: Article
Language:English
Subjects:
cycloaddition reactions
photocatalysis
photocatalysts
regioselectivity
ultraviolet radiation
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A facile and efficient radical tandem vinylogous aldol and intramolecular [2 + 2] cycloaddition reaction for direct synthesis of cyclobutane-containing benzocyclobutenes (BCBs) under extremely mild conditions without using any photocatalysts is reported. This approach exhibited definite compatibility with functional groups and afforded new BCBs with excellent regioselectivity and high yields. Moreover, detailed mechanism studies were carried out both experimentally and theoretically. The readily accessible, low-cost, and ecofriendly nature of the developed strategy will endow it with attractive applications in organic and medicinal chemistry.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00994