Spectroscopic Investigation of the Remote C–H Allylation of Amides via Photoredox and Nickel Dual Catalysis

Bourgois, Céline;De Kreijger, Simon;Xu, Bin;Tambar, Uttam K.;Troian-Gautier, Ludovic
(2024) Synlett : accounts and rapid communications in synthetic organic chemistry — Vol. 35, p. A-F (2024)

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The mechanistic details of a reported allylation reaction are investigated by means of Stern–Volmer experiments and nanosecond transient absorption spectroscopy. Both reference substrates, i.e., an allylic chloride and a trifluoroacetamide, are inefficient quenchers but large quenching rate constants are observed upon the addition of Ni(COD)2 and a bisoxazoline ligand. The large quenching rate constants and absence of observable photoproducts are consistent with a mechanism that operates by energy transfer between the excited-state iridium photosensitizer and the nickel complex.
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Bourgois, C., De Kreijger, S., Xu, B., Tambar, U. K., & Troian-Gautier, L. (2024). Spectroscopic Investigation of the Remote C–H Allylation of Amides via Photoredox and Nickel Dual Catalysis. Synlett : accounts and rapid communications in synthetic organic chemistry, 35, A-F. https://doi.org/10.1055/a-2259-3594 (Original work published 2024)