{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Yao W"],"funding":["Shimadzu","Division of Advanced Cyberinfrastructure","Office of the Vice President for Research, Stony Brook University","National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["3353-3359"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8970705"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["144(8)"],"pubmed_abstract":["Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex molecular architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the p"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates."],"pmcid":["PMC8970705"],"funding_grant_id":["R35 GM128779","R35-GM119652-04S1","R35-GM119652","R35 GM119652","ACI1548562","R35-GM128779"],"pubmed_authors":["Zhou L","Zhao G","Liu P","Ngai MY","Yao W","Wu Y","Mukherjee U"],"additional_accession":[]},"is_claimable":false,"name":"Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates.","description":"Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex molecular architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the p","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Mar","modification":"2025-04-26T10:21:11.937Z","creation":"2025-04-06T13:17:57.072Z"},"accession":"S-EPMC8970705","cross_references":{"pubmed":["35188768"],"doi":["10.1021/jacs.1c13299"]}}