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Updated: Feb 9, 2026
Millifluidics for Chemical Synthesis and Time-resolved Mechanistic Studies
Published on: November 27, 2013
Cobalt-Catalyzed Stereoselective Synthesis of 2,5- trans-THF Nitrile Derivatives as a Platform for Diversification:
Sajjad Ali1, Henrique Milanezi1, Tânia M F Alves1
1Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry , Federal University of São Carlos - UFSCar , São Carlos, São Paulo 13565-905 , Brazil.
Abstract:
A straightforward protocol integrating a sustainable approach for the synthesis of new 2,5- trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substituents, affording the corresponding 2,5- trans-THFs in high diastereoselectivity. A detailed mechanistic study using DFT calculation reveals details of the ligand-exchange step, suggesting an inner-sphere syn attack to form the 2,5- trans stereochemistry as the most likely pathway, excluding the previous cation radical intermediate. The formation of a Co-C intermediate is suggested on the basis of the homolytic cleavage to give the previously proposed free carbon radical intermediate.
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