Issue 36, 2020
From the journal:

Organic & Biomolecular Chemistry

Cu(i)-Catalyzed addition–cycloisomerization difunctionalization reaction of 1,3-enyne-alkylidenecyclopropanes (ACPs)†

Peng-Hua Li,ab   Yin Weia  and  Min Shi ORCID logo *ab  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: mshi@mail.sioc.ac.cn

b Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China

Abstract

A copper(I)-catalyzed three-component addition–cycloisomerization difunctionalization reaction of 1,3-enyne-ACPs with Togni I reagent and TMSCN under mild reaction conditions has been developed, affording 3-trifluoroethylcyclopenta[b]naphthalene-4-carbonitrile derivatives. The reaction proceeded through a copper(I)-catalyzed 1,4-addition of conjugated 1,3-enynes via a radical relay process and aromatic cycloisomerization of allene–ACP intermediates.

Graphical abstract: Cu(i)-Catalyzed addition–cycloisomerization difunctionalization reaction of 1,3-enyne-alkylidenecyclopropanes (ACPs)

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Article information

DOI
https://doi.org/10.1039/D0OB01692F
Article type
Paper
Submitted
16 Aug 2020
Accepted
26 Aug 2020
First published
26 Aug 2020

Org. Biomol. Chem., 2020,18, 7127-7138

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Cu(I)-Catalyzed addition–cycloisomerization difunctionalization reaction of 1,3-enyne-alkylidenecyclopropanes (ACPs)

P. Li, Y. Wei and M. Shi, Org. Biomol. Chem., 2020, 18, 7127 DOI: 10.1039/D0OB01692F

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