The transient-chelating-group-controlled stereoselective Rh(I)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones

Ya-Fei Han; Gui-Fen Lv; Yang Li; Li-Jun Wu; Xuan-Hui Ouyang; Jin-Heng Li

doi:10.1039/D2SC03009H

The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones†

Ya-Fei Han,^a Gui-Fen Lv,^a Yang Li,

*^a Li-Jun Wu,*^b Xuan-Hui Ouyang

^a and Jin-Heng Li

*^acde

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* Corresponding authors

^a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
E-mail: liyang8825490@126.com, jhli@hnu.edu.cn

^b College of Sciences, Central South University of Forestry and Technology, Changsha, China
E-mail: lijunwu1105@hnu.edu.cn

^c Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, China

^d State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

^e School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China

Abstract

A new method involving mild acryl transient-chelating-group-controlled stereoselective Rh(I)-catalyzed silylative aminocarbonylation of 2-alkynylanilines with CO and silanes is presented for producing (Z)-3-(silylmethylene)indolin-2-ones. Upon using an acryl transient chelating group, 2-alkynylanilines undergo an unprecedented alkyne cis-silylrhodation followed by aminocarbonylation to assemble (Z)-3-(silylmethylene)indolin-2-ones. Mechanistic studies show that acryl transient chelating effects result in the key alkyne cis-silylrhodation process.

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DOI: https://doi.org/10.1039/D2SC03009H
Article type: Edge Article
Submitted: 30 May 2022
Accepted: 27 Jul 2022
First published: 27 Jul 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2022,13, 9425-9431

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The transient-chelating-group-controlled stereoselective Rh(I)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones

Y. Han, G. Lv, Y. Li, L. Wu, X. Ouyang and J. Li, Chem. Sci., 2022, 13, 9425 DOI: 10.1039/D2SC03009H

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Chemical Science

The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones†

Abstract

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The transient-chelating-group-controlled stereoselective Rh(I)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones

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