{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Zhang J"],"funding":["Research Grants Council, University Grants Committee","Chinese University of Hong Kong"],"pagination":["9925-9929"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8162123"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["11(36)"],"pubmed_abstract":["This work reports an unprecedented cascade cyclization of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes promoted by magnesium-mediated sp<sup>3</sup> C-H activation. Treatment of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes with MeMgBr gives a series of carborane-fused cyclopentanes in very good yields. Deuterium labelling and control experiments suggest that HMgBr, resulting <i>in situ</i> from the nucleophilic substitution of cage B-H bonds with Grignard reagent, initiates the reaction, in which magnesium-promoted intramolecular sp<sup>3</sup> C-H activation serves as a key step. This work not only offers a new route for the synthesis of carborane-fused cyclopentanes, but also sheds some light on Mg-mediated C-H activation and functionalization."],"journal":["Chemical science"],"pubmed_title":["Magnesium-mediated sp<sup>3</sup> C-H activation in cascade cyclization of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes: efficient synthesis of carborane-fused cyclopentanes."],"pmcid":["PMC8162123"],"funding_grant_id":["14305918"],"pubmed_authors":["Zhang J","Xie Z","Tang C"],"additional_accession":[]},"is_claimable":false,"name":"Magnesium-mediated sp<sup>3</sup> C-H activation in cascade cyclization of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes: efficient synthesis of carborane-fused cyclopentanes.","description":"This work reports an unprecedented cascade cyclization of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes promoted by magnesium-mediated sp<sup>3</sup> C-H activation. Treatment of 1-arylethynyl-2-alkyl-<i>o</i>-carboranes with MeMgBr gives a series of carborane-fused cyclopentanes in very good yields. Deuterium labelling and control experiments suggest that HMgBr, resulting <i>in situ</i> from the nucleophilic substitution of cage B-H bonds with Grignard reagent, initiates the reaction, in which magnesium-promoted intramolecular sp<sup>3</sup> C-H activation serves as a key step. This work not only offers a new route for the synthesis of carborane-fused cyclopentanes, but also sheds some light on Mg-mediated C-H activation and functionalization.","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Sep","modification":"2025-04-04T08:18:21.5Z","creation":"2022-02-10T13:57:56.494Z"},"accession":"S-EPMC8162123","cross_references":{"pubmed":["34094253"],"doi":["10.1039/d0sc04465b"]}}