AI Article Synopsis
- A new method to create N-substituted 2-amino-2'-hydroxy-1,1'-biaryls was found using aryne chemistry with indolyl β-ketonitrile/ester in a sequence of reactions.
- The process consists of a series of steps including cycloaddition, cleavage, and an intramolecular addition without the use of transition metals.
- Despite the potential for a [4 + 2] Diels-Alder reaction to occur, researchers did not find any evidence of the expected product in this experiment.
Article Abstract
A serendipitous synthesis of N-substituted 2-amino-2'-hydroxy-1,1'-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
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| http://dx.doi.org/10.1021/acs.orglett.0c02749 | DOI Listing |
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