biostudies-literaturePolites VCDivision of ChemistryBristol-Myers SquibbNational Institute of General Medical SciencesNIGMS NIH HHS4828-4833https://www.ebi.ac.uk/biostudies/studies/S-EPMC8917872biostudies-literatureUnknown23(12)The use of bicyclo[1.1.1]pentanes (BCPs) as <i>para</i>-disubstituted aryl bioisosteres has gained considerable momentum in drug development programs. Carbon-carbon bond formation via transition-metal-mediated cross-coupling represents an attractive strategy to generate BCP-aryl compounds for late-stage functionalization, but these typically require reactive organometallics to prepare BCP nucleophiles on demand from [1.1.1]propellane. In this study, the synthesis and Ni-catalyzed functionalization of BCP redox-active esters with (hetero)aryl bromides via the action of a photoactive electron donor-acceptor complex are reported.Organic lettersNickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation.PMC8917872R01 GM087605NSF CHE-1827457R01GM087605-06S1R01GM118510-03S1R01 GM118510R35 GM 131680R35 GM131680Badir SOPolites VCMolander GAJolit AKeess SfalseNickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation.The use of bicyclo[1.1.1]pentanes (BCPs) as <i>para</i>-disubstituted aryl bioisosteres has gained considerable momentum in drug development programs. Carbon-carbon bond formation via transition-metal-mediated cross-coupling represents an attractive strategy to generate BCP-aryl compounds for late-stage functionalization, but these typically require reactive organometallics to prepare BCP nucleophiles on demand from [1.1.1]propellane. In this study, the synthesis and Ni-catalyzed functionalization of BCP redox-active esters with (hetero)aryl bromides via the action of a photoactive electron donor-acceptor complex are reported.2021-01-01T00:00:00Z2021 Jun2025-04-19T17:38:24.441Z2025-04-19T17:38:24.441ZS-EPMC89178723410062410.1021/acs.orglett.1c01558