A Typical NEDDA Cycloaddition Strategy between C-3- and N-Substituted Indoles and Butadienes Using Silica-supported Copper Triflate as an Efficient Catalytic System

The present paper elicits a [4+2] Diels-Alder cycloaddition strategy between C-3- and N-substituted indoles I-1 to I-6 with two dienes of different nucleophilicity using silica-supported Cu(OTf)2. Theoretical studies computed at the B3LYP/6-311G(d) level of theory reveal that all the indoles underta...

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Bibliographic Details
Published in:Chemistry letters 2016-07, Vol.45 (7), p.752-752
Main Authors: Ahuja, Monika, Kour Reen, Gagandeep, Kumar, Ashok, Sharma, Pratibha
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Computation
Copper
Cycloaddition
Indoles
Pathways
Strategy
Online Access:Get full text
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Summary:The present paper elicits a [4+2] Diels-Alder cycloaddition strategy between C-3- and N-substituted indoles I-1 to I-6 with two dienes of different nucleophilicity using silica-supported Cu(OTf)2. Theoretical studies computed at the B3LYP/6-311G(d) level of theory reveal that all the indoles undertaken behave as electron-poor dienophiles and, therefore, prefer to participate through a normal electron demand Diels-Alder (NEDDA) pathway. The analysis of the local reactivity descriptors further ascertained the completely regioselective outcome of the reaction profile.
ISSN:0366-7022
1348-0715