{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Zhang Z"],"funding":["University of Chicago","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["21096-21103"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11102776"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["145(38)"],"pubmed_abstract":["Alkyl halides are versatile precursors to access diverse functional groups (FGs). Due to their lability, the development of surrogates for alkyl halides is strategically important for complex molecule synthesis. Given the stability and ease of derivatization inherent in common alkyl ketones, here we report a deacylative halogenation approach to convert various methyl ketones to the corresponding alkyl chlorides, bromides, and iodides. The reaction is driven by forming an aromatic byproduct, i.e., 1,2,4-triazole, in which <i>N</i>'-methylpicolinohydrazonamide (MPHA) is employed to form a prearomatic intermediate and halogen atom-transfer (XAT) reagents are used to quench the alkyl radical intermediate. The reaction is efficient in yielding primary and secondary alkyl halides from a wide ran"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Methyl Ketones as Alkyl Halide Surrogates: A Deacylative Halogenation Approach for Strategic Functional Group Conversions."],"pmcid":["PMC11102776"],"funding_grant_id":["R01 GM109054","2R01GM109054"],"pubmed_authors":["Dong G","Zhang Z","Pyle D","Zhu Q","Zhou X"],"additional_accession":[]},"is_claimable":false,"name":"Methyl Ketones as Alkyl Halide Surrogates: A Deacylative Halogenation Approach for Strategic Functional Group Conversions.","description":"Alkyl halides are versatile precursors to access diverse functional groups (FGs). Due to their lability, the development of surrogates for alkyl halides is strategically important for complex molecule synthesis. Given the stability and ease of derivatization inherent in common alkyl ketones, here we report a deacylative halogenation approach to convert various methyl ketones to the corresponding alkyl chlorides, bromides, and iodides. The reaction is driven by forming an aromatic byproduct, i.e., 1,2,4-triazole, in which <i>N</i>'-methylpicolinohydrazonamide (MPHA) is employed to form a prearomatic intermediate and halogen atom-transfer (XAT) reagents are used to quench the alkyl radical intermediate. The reaction is efficient in yielding primary and secondary alkyl halides from a wide ran","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Sep","modification":"2025-04-04T09:48:51.725Z","creation":"2025-04-04T09:48:51.725Z"},"accession":"S-EPMC11102776","cross_references":{"pubmed":["37712624"],"doi":["10.1021/jacs.3c08176"]}}