Synthesis of 3-aminoindenes and cis-1-aminoindanes by Zn(OTf)2-catalyzed cyclization of o-alkynylbenzaldehydes with tertiary alkyl primary amines

Tuanli Yao; Rui Zhu; Tao Liu

doi:10.1039/D3CC04180H

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Synthesis of 3-aminoindenes and cis-1-aminoindanes by Zn(OTf)₂-catalyzed cyclization of o-alkynylbenzaldehydes with tertiary alkyl primary amines†

Tuanli Yao,

*^a Rui Zhu^a and Tao Liu^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an, China
E-mail: yaotuanli@sust.edu.cn

Abstract

Using Zn(OTf)₂ as catalyst, a highly regio- and chemo-selective cyclocarboamination of o-alkynylbenzaldehydes with tertiary alkyl primary amines was realized to access 3-aminoindenes with different substitution patterns from previously reported methods. The full reduction of the iminoindenone intermediates affords cis-1-amino-2-arylindanes with excellent diastereoselectivity. Mechanistically, the reaction involves the rearrangement of 1-amino-3-arylidene-isoindolines and isomerization of 1-aminoindenes to 3-aminoindenes.

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Article information

DOI: https://doi.org/10.1039/D3CC04180H
Article type: Communication
Submitted: 26 Aug 2023
Accepted: 03 Nov 2023
First published: 06 Nov 2023

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Chem. Commun., 2023,59, 14325-14328

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Synthesis of 3-aminoindenes and cis-1-aminoindanes by Zn(OTf)₂-catalyzed cyclization of o-alkynylbenzaldehydes with tertiary alkyl primary amines

T. Yao, R. Zhu and T. Liu, Chem. Commun., 2023, 59, 14325 DOI: 10.1039/D3CC04180H

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Chemical Communications