Decarboxylative C(sp 2 )−C(sp 3 ) Cross-Coupling of Bicyclo[1.1.1]pentane and Cubane Carboxylic Acids Using a Nickel(II) Aryl Precatalyst
Year: 2026
Type: article
Abstract: Metallaphotoredox conditions employing an iridium photocatalyst and a nickel(II) oxidative addition complex as a precatalyst have been developed for the elusive direct decarboxylative C(sp2)–C(sp3) cross-coupling of bicyclo[1.1.1]pentane carboxylic acids and cubane carboxylic acids with (hetero)aryl halides. The substrate scope is broad, and the reaction is applicable to late-stage functionalization of complex, pharmaceutically relevant substrates. NMR experiments provide insight into how the nickel(II) oxidative addition complex enters the catalytic cycle and suggest it achieves the proposed catalyst resting state more efficiently than a more commonly used ligated nickel(II) bromide salt. This study is the first example of a catalytic nickel(II) oxidative addition complex being used in metallaphotoredox method development and the first example of a cubane carboxylic acid directly engaging in C(sp2)–C(sp3) cross-coupling.
Source: ACS Catalysis
Institution: Bristol-Myers Squibb (United States)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7160835131