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Synlett 2013; 24(14): 1842-1844
DOI: 10.1055/s-0033-1339510
DOI: 10.1055/s-0033-1339510
letter
Rhodium(III)-Catalyzed C–H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes
Further Information
Publication History
Received: 11 June 2013
Accepted after revision: 14 July 2013
Publication Date:
08 August 2013 (online)
Abstract
We have developed a synthesis of 4-substituted isoquinolones from the rhodium(III)-catalyzed, C–H activation mediated coupling of O-pivaloyl benzhydroxamic acids and 3,3-disubstituted cyclopropenes. Experiments suggest the formation of a [4.1.0] bicyclic system, which can open under acidic conditions to generate the desired isoquinolone.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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- 9 General Procedure for the Synthesis of 3a A 1.5 dram vial was charged with a stir bar, 1a (0.2 mmol), [RhCp*Cl2]2 (1 mol %), CsOAc (0.4 mmol), and MeOH (1 mL). After stirring for 30 s, cyclopropene 2a (0.22 mmol) was added, and the reaction mixture was allowed to stir for 8 h at 23 °C. Upon completion, as determined by TLC, the reaction mixture was concentrated. The crude residue was purified via column chromatography (2:1 hexanes–EtOAc with 1% Et3N) to provide the isoquinolone 3a as a white solid (99% yield).