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

Abstract

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.

Key words

photoredox - energy transfer - mechanism - iridium - transient absorption - quenching - Stern–Volmer

Publication History

Received: 15 December 2023

Accepted after revision: 01 February 2024

Accepted Manuscript online:
01 February 2024

Article published online:
23 February 2024

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