Indolizine Synthesis through Annulation of Pyridinium 1,4‐Thiolates and Copper Carbenes: A Predictive Catalysis Approach

Predictive catalysis was applied to the reaction of pyridinium 1,4‐zwitterionic thiolates with a copper carbene. Theoretical calculations were first performed to determine the suitability of their annulation reaction and to make predictions about the performance of different copper salts, diazo spec...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-03, Vol.365 (5), p.760-766
Main Authors: Monreal‐Corona, Roger, Díaz‐Jiménez, Àlex, Roglans, Anna, Poater, Albert, Pla‐Quintana, Anna
Format: Article
Language:English
Subjects:
Carbene
Carbenes
Catalysis
Chemical reactions
Chemical synthesis
Copper
DFT
Indolizine
Mathematical analysis
Organic chemistry
Predictive catalysis
Zwitterions
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Summary:Predictive catalysis was applied to the reaction of pyridinium 1,4‐zwitterionic thiolates with a copper carbene. Theoretical calculations were first performed to determine the suitability of their annulation reaction and to make predictions about the performance of different copper salts, diazo species, and pyridinium derivatives. With calculations in hand, the experimental conditions were optimized, the scope of the reaction was assessed, and the precision of the predictions was evaluated. Yields up to 90% were obtained for the synthesis of indolizine scaffolds in the reactivity of pyridinium 1,4‐zwitterionic thiolates with a metal carbene.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201277