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Synlett 2024; 35(16): 1893-1898
DOI: 10.1055/a-2259-3594
DOI: 10.1055/a-2259-3594
letter
Special Section 14th EuCheMS Organic Division Young Investigator Workshop
Spectroscopic Investigation of the Remote C–H Allylation of Amides via Photoredox and Nickel Dual Catalysis
L.T.-G. is a Chercheur Qualifié of the Fonds de la Recherche Scientifique - FNRS. C.B., S.D.K. and L.T.-G. gratefully acknowledge the Université catholique de Louvain for financial support. Financial support was provided to U.K.T by a W. W. Caruth, Jr. Endowed Scholarship, Welch Foundation (I-1748), the National Institutes of Health (R01GM102604), and Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV).
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–VolmerSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2259-3594.
- Supporting Information
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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