{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Amber C"],"funding":["NIGMS NIH HHS"],"pagination":["17655-17663"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11624976"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["89(23)"],"pubmed_abstract":["Given its relevance across numerous fields, reductive amination is one of the oldest and most widely used methods for amine synthesis. As a cornerstone of synthetic chemistry, it has largely remained unchanged since its discovery over a century ago. Herein, we report the mechanistically driven development of a complementary reaction, which reductively aminates the C-C σ-bond of carbonyls, not the carbonyl C-O π-bond, generating value-added linear and cyclic 3° amines in a modular fashion. Critical to our success were mechanistic insights that enabled us to modulate the resting state of a borane catalyst, minimize deleterious disproportionation of a hydroxylamine nitrogen source, and control the migratory selectivity of a key nitrenoid reactive intermediate. Experiments support the reaction"],"journal":["The Journal of organic chemistry"],"pubmed_title":["Reductive Amination of Carbonyl C-C Bonds Enables Formal Nitrogen Insertion."],"pmcid":["PMC11624976"],"funding_grant_id":["R35 GM130345"],"pubmed_authors":["Petitjean TM","Sarpong R","Gottemann LT","Amber C","Steele RT"],"additional_accession":[]},"is_claimable":false,"name":"Reductive Amination of Carbonyl C-C Bonds Enables Formal Nitrogen Insertion.","description":"Given its relevance across numerous fields, reductive amination is one of the oldest and most widely used methods for amine synthesis. As a cornerstone of synthetic chemistry, it has largely remained unchanged since its discovery over a century ago. Herein, we report the mechanistically driven development of a complementary reaction, which reductively aminates the C-C σ-bond of carbonyls, not the carbonyl C-O π-bond, generating value-added linear and cyclic 3° amines in a modular fashion. Critical to our success were mechanistic insights that enabled us to modulate the resting state of a borane catalyst, minimize deleterious disproportionation of a hydroxylamine nitrogen source, and control the migratory selectivity of a key nitrenoid reactive intermediate. Experiments support the reaction","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Dec","modification":"2025-04-18T13:08:37.502Z","creation":"2025-04-06T22:40:37.151Z"},"accession":"S-EPMC11624976","cross_references":{"pubmed":["39509344"],"doi":["10.1021/acs.joc.4c02400"]}}