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Divergent Syntheses of Spiroindanones and 2-Substituted 1-Indanones by Ruthenium-Catalyzed Tandem Coupling and Cyclization of Aromatic Acids with α,β-Unsaturated Ketones

Authors :
Xian-Ying Shi
Zhong-Wen Liu
Si-Qi Chen
Jia-Ni Wang
Source :
The Journal of Organic Chemistry. 84:1348-1362
Publication Year :
2019
Publisher :
American Chemical Society (ACS), 2019.

Abstract

The one-step strategy for the facile syntheses of structurally diverse 1-indanones in moderate to good isolated yields was developed via a ruthenium-catalyzed tandem coupling and cyclization of simple aromatic acids with α,β-unsaturated ketones. The tandem cyclization involves one-pot sequential reactions of C–H activation, conjugate addition, Dieckmann condensation, Michael addition, intramolecular Aldol reaction, or hydrolysis. Switchable access to spiroindanones and 2-substituted 1-indanones could be achieved by manganese additive and H2O. Mn(II) additive is found to play an important role in this transformation, and a trace amount of water can promote the formation of 2-substituted 1-indanones. This process features the one-pot efficient construction of multiple C–C bonds, high step-economy, commercially available starting materials, and a broad substrate scope.

Details

ISSN :
15206904 and 00223263
Volume :
84
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....c38fa75d8c63e03265491e37ba4441dd
Full Text :
https://doi.org/10.1021/acs.joc.8b02820