Issue 43, 2018
From the journal:

Chemical Science

Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol†

Shuai-Shuai Li, ORCID logo a   Xintong Lv,a   Didi Ren,a   Chang-Lun Shao,b   Qing Liuc  and  Jian Xiao ORCID logo *a  

* Corresponding authors

a Shandong Province Key Laboratory of Applied Mycology, College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, China
E-mail: chemjianxiao@163.com

b Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China

c College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590, China

Abstract

An unprecedented cascade dearomative cyclization through hydrogen-bonding-assisted hydride transfer is realized. The aggregate effect of HFIP enables the rapid buildup of polycyclic amines directly from phenols and o-aminobenzaldehydes via a cascade dearomatization/rearomatization/dearomatization sequence. This unique transformation addressed the drawbacks of hydride transfer-involved redox-neutral reactions.

Graphical abstract: Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol

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Article information

DOI
https://doi.org/10.1039/C8SC03339K
Article type
Edge Article
Submitted
27 Jul 2018
Accepted
31 Aug 2018
First published
13 Sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 8253-8259

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Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol

S. Li, X. Lv, D. Ren, C. Shao, Q. Liu and J. Xiao, Chem. Sci., 2018, 9, 8253 DOI: 10.1039/C8SC03339K

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