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Au(I)-Catalyzed 6-endo-dig Cyclizations of Aromatic 1,5-Enynes to 2-(Naphthalen-2-yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives

15 July 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A gold(I)-catalyzed 6-endo-dig cyclization of aromatic 1,5-enyne was developed to synthesize 2-(naphthalen-2-yl)aniline. The functional group tolerance of this cyclization was examined systematically and a possible mechanism was proposed. The derivatization of 2-(naphthalen-2-yl)aniline was carried out to facile access to benzo[α]carbazole, benzo[c,h]cinnoline and dibenzo[i]phenanthridine derivatives in a divergent way.

Keywords

gold catalysis
divergent syntheses
aniline cyclization

Supplementary materials

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Title
The supporting information for the manuscript entitled "Au(I)-Catalyzed 6-endo-dig Cyclizations of Aromatic 1,5-Enynes to 2-(Naphthalen-2-yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives"
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the NMR spectra for all the compounds in the manuscript
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Now Published

Au(I)‐Catalyzed 6‐ endo ‐ dig Cyclizations of Aromatic 1, 5‐Enynes to 2‐(Naphthalen‐2‐yl)anilines Leading to Divergent Syntheses of Benzo[ α ]carbazole, Benzo[ c , h ]cinnoline and Dibenzo[ i ]phenanthridine Derivatives [opens in a new tab]
Jiayue Fu, Bingbing Li, Xiugui Wang, Qida Liang, Xiaoshi Peng, Lu Yang, Tao Wan, Xinxiu Wang, Bin Lin, Maosheng Cheng, Yongxiang Liu journal article
Chinese Journal of Chemistry , Volume 40, Issue 1
Online publication date: Nov 16, 2021

Version History

Jul 15, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-fs5qw
D O I: 10.26434/chemrxiv-2021-fs5qw [opens in a new tab]

Funding

National Natural Science Foundation of China
21977073

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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