Mechanistic insights into excited-state palladium catalysis for C–S bond formations and dehydrogenative sulfonylation of amines

Krishnamoorthy Muralirajan, Rajesh Kancherla, Bholanath Maity, Safakath Karuthedath, Frédéric Laquai (), Luigi Cavallo () and Magnus Rueping ()
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Krishnamoorthy Muralirajan: King Abdullah University of Science and Technology (KAUST)
Rajesh Kancherla: 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)
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, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract Photocatalytic selective C(sp3)–H activation/cross-coupling reactions are appealing in organic synthesis. In this manuscript, we describe the development of photoexcited-state Pd-catalyzed dehydrogenative β-sulfonylation reactions using amines and aryl sulfonyl chlorides via intermolecular hydrogen atom transfer and C−S cross-coupling processes at room temperature. The transformation can be achieved by the direct generation of two distinct Pd-radical hybrid species and their capability to promote two different reactivities from Pd(0) and aryl sulfonyl chlorides, allowing for the efficient conversion of readily available amines into stable sulfonyl-substituted enamines at room temperature. The in-depth experimental, computational, and transient optical spectroscopic study and catalytic applications of a dehydrogenative functionalization event provide evidence for both static and dynamic quenching, as well as inner-sphere and outer-sphere mechanisms.

Date: 2023
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DOI: 10.1038/s41467-023-42392-2

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