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

被引:0
作者
Bourgois, Celine [1 ]
De Kreijger, Simon [1 ]
Xu, Bin [2 ]
Tambar, Uttam K. [2 ]
Troian-Gautier, Ludovic [1 ,3 ]
机构
[1] Univ Catholique Louvain UCLouvain, Inst Matiere Condensee & Nanosci IMCN, Mol Chem Mat & Catalysis MOST, Pl Louis Pasteur 1,Bte L4 01-02, B-1348 Louvain La Neuve, Belgium
[2] Univ Texas Southwestern Med Ctr Dallas, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USA
[3] Wel Res Inst, Ave Pasteur 6, B-1300 Wavre, Belgium
关键词
photoredox; energy transfer; mechanism; iridium; transient absorption; quenching; Stern-Volmer; SUBSTITUTION; COMPLEXES; PHOTOCHEMISTRY; RELEASE; BINDING; BONDS; TIO2;
D O I
10.1055/a-2259-3594
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The mechanistic details of a reported allylation reaction are investigated by means of Stern-Volmer experiments and nano second transient absorption spectroscopy. Both reference substrates, i.e., an allylic chloride and a trifluoroacetamide, are inefficient quenchers butlarge 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
引用
收藏
页码:1893 / 1898
页数:6
相关论文
共 51 条
[1]   Ligand Coordination and Spin Crossover in a Nickel Porphyrin Anchored to Mesoporous TiO2 Thin Films [J].
Achey, Darren ;
Meyer, Gerald J. .
INORGANIC CHEMISTRY, 2013, 52 (16) :9574-9582
[2]   The photophysics of photoredox catalysis: a roadmap for catalyst design [J].
Arias-Rotondo, Daniela M. ;
McCusker, James K. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (21) :5803-5820
[3]   Mechanistic investigation of a visible light mediated dehalogenation/cyclisation reaction using iron(iii), iridium(iii) and ruthenium(ii) photosensitizers [J].
Aydogan, Akin ;
Bangle, Rachel E. ;
De Kreijger, Simon ;
Dickenson, John C. ;
Singleton, Michael L. ;
Cauet, Emilie ;
Cadranel, Alejandro ;
Meyer, Gerald J. ;
Elias, Benjamin ;
Sampaio, Renato N. ;
Troian-Gautier, Ludovic .
CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (24) :8037-8051
[4]   Accessing Photoredox Transformations with an Iron(III) Photosensitizer and Green Light [J].
Aydogan, Akin ;
Bangle, Rachel E. ;
Cadranel, Alejandro ;
Turlington, Michael D. ;
Conroy, Daniel T. ;
Cauet, Emilie ;
Singleton, Michael L. ;
Meyer, Gerald J. ;
Sampaio, Renato N. ;
Elias, Benjamin ;
Troian-Gautier, Ludovic .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (38) :15661-15673
[5]   A Roadmap Towards Visible Light Mediated Electron Transfer Chemistry with Iridium(III) Complexes [J].
Bevernaegie, Robin ;
Wehlin, Sara A. M. ;
Elias, Benjamin ;
Troian-Gautier, Ludovic .
CHEMPHOTOCHEM, 2021, 5 (03) :217-234
[6]   Ultrafast charge transfer excited state dynamics in trifluoromethyl-substituted iridium(III) complexes [J].
Bevernaegie, Robin ;
Marcelis, Lionel ;
Moreno-Betancourt, Angelica ;
Laramee-Milette, Baptiste ;
Hanan, Garry S. ;
Loiseau, Frederique ;
Sliwa, Michel ;
Elias, Benjamin .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2018, 20 (43) :27256-27260
[7]   Shedding Light on the Oxidizing Properties of Spin-Flip Excited States in a CrIII Polypyridine Complex and Their Use in Photoredox Catalysis [J].
Burgin, Tobias H. ;
Glaser, Felix ;
Wenger, Oliver S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (31) :14181-14194
[8]   Photostable Polynuclear Ruthenium(II) Photosensitizers Competent for Dehalogenation Photoredox Catalysis at 590 nm [J].
Cerfontaine, Simon ;
Wehlin, Sara A. M. ;
Elias, Benjamin ;
Troian-Gautier, Ludovic .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5549-5555
[9]   Spectroscopic Techniques to Unravel Mechanistic Details in Light-Induced Transformations and Photoredox Catalysis [J].
De Kreijger, Simon ;
Gillard, Martin ;
Elias, Benjamin ;
Troian-Gautier, Ludovic .
CHEMCATCHEM, 2024, 16 (01)
[10]   Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers [J].
De Kreijger, Simon ;
Elias, Benjamin ;
Troian-Gautier, Ludovic .
INORGANIC CHEMISTRY, 2023, 62 (39) :16196-16202