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Synthesis 2017; 49(16): 3609-3618
DOI: 10.1055/s-0036-1588820
DOI: 10.1055/s-0036-1588820
paper
Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Brønsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones
We thank the National Natural Science Foundation of China (Grant No. 21272074) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) for financial support.Further Information
Publication History
Received: 13 March 2017
Accepted after revision: 01 April 2017
Publication Date:
09 May 2017 (online)
Abstract
A novel gold(I)/Brønsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Brønsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp2)-H functionalization of enaminones and Brønsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.
Key words
gold(I) catalysis - Brønsted acid promotion - C(sp2)–H functionalization - carbon–carbon bond activation - one-pot synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588820.
- Supporting Information
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