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

Viktor C. Polites | Zendy; Shorouk O. Badir | Zendy; Sebastian Keeß | Zendy; Anaïs Jolit | Zendy; Gary A. Molander | Zendy

Open Access

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

Author(s) -

Viktor C. Polites,

Shorouk O. Badir,

Sebastian Keeß,

Anaïs Jolit,

Gary A. Molander

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01558

Subject(s) - chemistry , nickel , catalysis , radical , electron acceptor , photochemistry , coupling (piping) , acceptor , electron , bicyclic molecule , decarboxylation , electron donor , stereochemistry , organic chemistry , physics , condensed matter physics , mechanical engineering , quantum mechanics , engineering

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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