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

Céline Bourgois; Simon De Kreijger; Bin Xu; Uttam K. Tambar; Ludovic Troian-Gautier

doi:10.1055/a-2259-3594

Synlett, Table of Contents

Synlett 2024; 35(16): 1893-1898
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

Céline Bourgois

^aUniversité catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium

,

Simon De Kreijger

^aUniversité catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium

,

Bin Xu

^bDepartment of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA

,

Uttam K. Tambar∗

^bDepartment of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA

,

Ludovic Troian-Gautier ∗

^aUniversité catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium

^cWel Research Institute, Avenue Pasteur 6, 1300 Wavre, Belgium

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Abstract

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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

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References

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