Open AccessNickel-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 , aryl , nucleophile , radical , catalysis , bicyclic molecule , electron acceptor , acceptor , combinatorial chemistry , surface modification , nickel , photochemistry , reactive intermediate , electron donor , organic chemistry , alkyl , physics , condensed matter physics
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.