Nickel-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 para-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 f...

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Bibliographic Details
Published in:Organic letters 2021-06, Vol.23 (12), p.4828-4833
Main Authors: Polites, Viktor C, Badir, Shorouk O, Keess, Sebastian, Jolit, Anais, Molander, Gary A
Format: Article
Language:English
Subjects:
Carbon - chemistry
Catalysis
Electrons
Esters
Molecular Structure
Nickel - chemistry
Oxidants
Oxidation-Reduction
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Summary:The use of bicyclo[1.1.1]­pentanes (BCPs) as para-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01558