Issue 82, 2018
From the journal:

Chemical Communications

Visible-light photocatalytic bicyclization of β-alkynyl propenones for accessing diastereoenriched syn-fluoren-9-ones†

Zheng-Jia Shen,a   Hao-Nan Shi,a   Wen-Juan Hao,*a   Shu-Jiang Tu ORCID logo *a  and  Bo Jiang ORCID logo *a  

* Corresponding authors

a School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, P. R. China
E-mail: jiangchem@jsnu.edu.cn, laotu@jsnu.edu.cn

Abstract

A novel visible-light photocatalytic bicyclization of β-alkynyl propenones with α-bromocarbonyls for highly diastereoselective synthesis of richly decorated syn-fluoren-9-ones is described. The reaction proceeds via a radical-triggered 5-exo-dig cyclization/1,6-H-abstraction/6-endo-trig cyclization cascade and offers a new and practical method for the assembly of 6/5/6 carbocyclic skeletons via C(sp3)–H alkenylation.

Graphical abstract: Visible-light photocatalytic bicyclization of β-alkynyl propenones for accessing diastereoenriched syn-fluoren-9-ones

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Article information

DOI
https://doi.org/10.1039/C8CC06086J
Article type
Communication
Submitted
26 iyl 2018
Accepted
28 avq 2018
First published
28 avq 2018

Chem. Commun., 2018,54, 11542-11545

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Visible-light photocatalytic bicyclization of β-alkynyl propenones for accessing diastereoenriched syn-fluoren-9-ones

Z. Shen, H. Shi, W. Hao, S. Tu and B. Jiang, Chem. Commun., 2018, 54, 11542 DOI: 10.1039/C8CC06086J

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