{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["6"],"submitter":["Chen WJ"],"pubmed_abstract":["Density functional theory calculations have been performed to study the detailed mechanism of Ni-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes via cleavage of two C-F bonds. It was found that the reaction pathway involves oxidative cyclization, the first <i>β</i>-fluorine elimination, and then intramolecular 5-<i>endo</i> insertion of difluoroalkene, followed by the second cleavage of C-F bond, and finally the dissociation of difluorides yields the fluorine-containing product cyclopentadienes in sequence. The overall rate-determining step is the combined processes of the β-fluorine elimination and the 5-<i>endo</i> insertion. Furthermore, we investigated the effect of different ligands and the regioselectivity of asymmetric alkynes. The detailed energy profiles a"],"journal":["Frontiers in chemistry"],"pagination":["319"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC6099089"],"repository":["biostudies-literature"],"pubmed_title":["DFT Studies on Ni-Mediated C-F Cleavage for the Synthesis of Cyclopentadiene Derivatives."],"pmcid":["PMC6099089"],"pubmed_authors":["Xu RN","Wang B","Wu QH","Huang X","Lin W","Sun X","Chen WJ"],"additional_accession":[]},"is_claimable":false,"name":"DFT Studies on Ni-Mediated C-F Cleavage for the Synthesis of Cyclopentadiene Derivatives.","description":"Density functional theory calculations have been performed to study the detailed mechanism of Ni-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes via cleavage of two C-F bonds. It was found that the reaction pathway involves oxidative cyclization, the first <i>β</i>-fluorine elimination, and then intramolecular 5-<i>endo</i> insertion of difluoroalkene, followed by the second cleavage of C-F bond, and finally the dissociation of difluorides yields the fluorine-containing product cyclopentadienes in sequence. The overall rate-determining step is the combined processes of the β-fluorine elimination and the 5-<i>endo</i> insertion. Furthermore, we investigated the effect of different ligands and the regioselectivity of asymmetric alkynes. The detailed energy profiles a","dates":{"release":"2018-01-01T00:00:00Z","publication":"2018","modification":"2025-04-19T06:28:03.811Z","creation":"2019-03-26T23:52:55Z"},"accession":"S-EPMC6099089","cross_references":{"pubmed":["30151361"],"doi":["10.3389/fchem.2018.00319"]}}