Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer

Rajesh Kancherla, Krishnamoorthy Muralirajan, Bholanath Maity, Safakath Karuthedath, Gadde Sathish Kumar, Frédéric Laquai, Luigi Cavallo and Magnus Rueping ()
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Rajesh Kancherla: King Abdullah University of Science and Technology (KAUST)
Krishnamoorthy Muralirajan: King Abdullah University of Science and Technology (KAUST)
Bholanath Maity: King Abdullah University of Science and Technology (KAUST)
Safakath Karuthedath: King Abdullah University of Science and Technology (KAUST)
Gadde Sathish Kumar: King Abdullah University of Science and Technology (KAUST)
Frédéric Laquai: King Abdullah University of Science and Technology (KAUST)
Luigi Cavallo: King Abdullah University of Science and Technology (KAUST)
Magnus Rueping: King Abdullah University of Science and Technology (KAUST)

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Various methods that use a photocatalyst for electron transfer between an organic substrate and a transition metal catalyst have been established. While triplet sensitization of organic substrates via energy transfer from photocatalysts has been demonstrated, the sensitization of transition metal catalysts is still in its infancy. Here, we describe the selective alkylation of C(sp3)–H bonds via triplet sensitization of nickel catalytic intermediates with a thorough elucidation of its reaction mechanism. Exergonic Dexter energy transfer from an iridium photosensitizer promotes the nickel catalyst to the triplet state, thus enabling C–H functionalization via the release of bromine radical. Computational studies and transient absorption experiments support that the reaction proceeds via the formation of triplet states of the organometallic nickel catalyst by energy transfer.

Date: 2022
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DOI: 10.1038/s41467-022-30278-8

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