4.8 Article

Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation

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ORGANIC LETTERS
卷 23, 期 12, 页码 4828-4833

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01558

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资金

  1. NIGMS [R35 GM 131680]
  2. Bristol-Myers Squibb
  3. National Science Foundation (NSF) Major Research Instrumentation Program [NSF CHE-1827457]
  4. National Institutes of Health (NIH) [3R01GM118510-03S1, 3R01GM087605-06S1]
  5. AbbVie

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This study reports 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.
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.

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