{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Meng X"],"funding":["College of Pharmacy, University of Arizona","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["8961-8966"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11527481"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["26(41)"],"pubmed_abstract":["We report a general approach for efficient deuteration of the metabolically labile α-C-H bonds of widespread amides and amines. Temporarily masking the secondary amine group as a carbamate allows an unprecedented photoredox hydrogen atom transfer-promoted α-carbamyl radical formation for efficient H/D exchange with D<sub>2</sub>O. The mild protocol delivers structurally diverse α-deuterated secondary amines including \"privileged\" piperidine and piperazine structures highly regioselectively with excellent levels of deuterium incorporation (≤100%). Furthermore, we successfully implemented the strategy for α-deuteration of amides, lactams, and ureas with high regioselectivity and high levels of D incorporation. Finally, the observed efficient deuteration of secondary alcohol moieties in late-"],"journal":["Organic letters"],"pubmed_title":["Organophotocatalytic Selective Deuteration of Metabolically Labile Heteroatom Adjacent C-H Bonds via H/D Exchange with D&lt;sub&gt;2&lt;/sub&gt;O."],"pmcid":["PMC11527481"],"funding_grant_id":["5R01GM125920","R01 GM125920"],"pubmed_authors":["Che C","Dong Y","Liu Q","Wang W","Meng X"],"additional_accession":[]},"is_claimable":false,"name":"Organophotocatalytic Selective Deuteration of Metabolically Labile Heteroatom Adjacent C-H Bonds via H/D Exchange with D&lt;sub&gt;2&lt;/sub&gt;O.","description":"We report a general approach for efficient deuteration of the metabolically labile α-C-H bonds of widespread amides and amines. Temporarily masking the secondary amine group as a carbamate allows an unprecedented photoredox hydrogen atom transfer-promoted α-carbamyl radical formation for efficient H/D exchange with D<sub>2</sub>O. The mild protocol delivers structurally diverse α-deuterated secondary amines including \"privileged\" piperidine and piperazine structures highly regioselectively with excellent levels of deuterium incorporation (≤100%). Furthermore, we successfully implemented the strategy for α-deuteration of amides, lactams, and ureas with high regioselectivity and high levels of D incorporation. Finally, the observed efficient deuteration of secondary alcohol moieties in late-","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Oct","modification":"2025-04-19T09:56:59.226Z","creation":"2025-04-19T09:56:59.226Z"},"accession":"S-EPMC11527481","cross_references":{"pubmed":["39374416"],"doi":["10.1021/acs.orglett.4c03493"]}}