Issue 14, 2018
From the journal:

Organic & Biomolecular Chemistry

Photocatalyzed cascade Meerwein addition/cyclization of N-benzylacrylamides toward azaspirocycles†

Li Yuan,‡a   Sheng-Ming Jiang,‡a   Zeng-Zeng Li,a   Yong Zhu,a   Jian Yu,a   Lan Li,a   Ming-Zhu Li,a   Shi Tang ORCID logo *a  and  Rui-Rong Shengbc  

* Corresponding authors

a College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. China
E-mail: stang@jsu.edu.cn

b CQM - Centro de Química da Madeira, Universidade da Madeira, Campus da Penteada, 9000-390 Funchal, Portugal

c Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, CAS. Lingling Road 345, Shanghai, P. R. China

Abstract

A visible-light-induced cascade Meerwein addition/cyclization of alkenes involving C–F bond cleavage was developed. This method offers a rapid access to azaspirocyclic cyclohexadienones from N-benzylacrylamides via C–F bond cleavage applying H2O as an external oxygen source, allowing for the incorporation of various aromatic moieties originating from aryldiazonium salts.

Graphical abstract: Photocatalyzed cascade Meerwein addition/cyclization of N-benzylacrylamides toward azaspirocycles

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Article information

DOI
https://doi.org/10.1039/C8OB00132D
Article type
Communication
Submitted
17 Jan 2018
Accepted
10 Mar 2018
First published
17 Mar 2018

Org. Biomol. Chem., 2018,16, 2406-2410

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Photocatalyzed cascade Meerwein addition/cyclization of N-benzylacrylamides toward azaspirocycles

L. Yuan, S. Jiang, Z. Li, Y. Zhu, J. Yu, L. Li, M. Li, S. Tang and R. Sheng, Org. Biomol. Chem., 2018, 16, 2406 DOI: 10.1039/C8OB00132D

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