4.8 Article

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

期刊

CHEMICAL SCIENCE
卷 13, 期 32, 页码 9425-9431

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc03009h

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资金

  1. National Natural Science Foundation of China [21871126]
  2. Jiangxi Province Science and Technology Project [20202ACB203002]
  3. Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University [2021ZD01]

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This article presents a new method for the production of (Z)-3-(silylmethylene)indolin-2-ones through a mild acryl transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines with CO and silanes. The use of an acryl transient chelating group leads to an unprecedented alkyne cis-silylrhodation followed by aminocarbonylation to assemble the desired products.
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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