Nickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes

Lin Guo, Watchara Srimontree, Chen Zhu, Bholanath Maity, Xiangqian Liu, Luigi Cavallo and Magnus Rueping ()
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Lin Guo: RWTH Aachen University
Watchara Srimontree: RWTH Aachen University
Chen Zhu: RWTH Aachen University
Bholanath Maity: King Abdullah University of Science and Technology (KAUST)
Xiangqian Liu: RWTH Aachen University
Luigi Cavallo: King Abdullah University of Science and Technology (KAUST)
Magnus Rueping: RWTH Aachen University

Nature Communications, 2019, vol. 10, issue 1, 1-6

Abstract: Abstract Transition-metal-catalyzed cross-couplings have been extensively used in the pharmaceutical and agrochemical industries for the construction of diverse C–C bonds. Conventional cross-coupling reactions require reactive electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly and not naturally abundant. Another disadvantage associated with these transformations is the need for an exogenous base to facilitate the key transmetalation step, and this reagent inevitably induces side reactions and limits the substrate scope. Here, we report an unconventional Suzuki-type approach to the synthesis of biaryls, through nickel-catalyzed deformylative cross coupling of aldehydes with organoboron reagents under base-free conditions. The transformation tolerates structurally diverse (hetero)aryl substituents on both coupling partners and shows high reactivity and excellent functional group tolerance. Furthermore, the protocol was carried out on gram scale and successfully applied to the functionalization of complex biologically active molecules. Mechanistic investigations support a catalytic cycle involving the oxidative addition of the nickel into the aldehyde C(acyl)–H bond with subsequent hydride transfer, transmetalation, decarbonylation and reductive elimination processes.

Date: 2019
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DOI: 10.1038/s41467-019-09766-x

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