Transition metal-mediated cross-coupling reactions are powerful tools for achieving chemoselective bond formation. However, despite advances in the field of cross-coupling chemistry, sp3–sp3 bond construction remains challenging, and as a result potential drug candidates have become limited to largely two-dimensional structures due to the ease of introducing sp2 carbons via traditional cross coupling reactions. Furthermore, current methodologies that achieve sp3-sp3 coupling often require the use of reactive organometallic reagents which can be undesirable in complex synthesis and generally require some prefunctionalization of starting materials (e.g., synthesis of organozinc reagents). Therefore, development of mild methodologies that can introduce three-dimensional complexity in a highly modular fashion without prefunctionalization would be highly beneficial for the field of chemical synthesis. Considering that nickel has proven successful for catalyzing sp3-sp3 cross couplings, we hoped to extend our dual photoredox-nickel catalysis platform to the longstanding challenge of sp3–sp3 cross-coupling, utilizing simple sp3 carboxylic acids as shown below in Figure 1.

Metallaphotoredox-catalysed cross-coupling of carboxylic acids with alkyl halides

255th National Meeting (2018)

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