Photosensitized Activation of Diazonium Derivatives for C-B Bond Formation.

Autor: Ripak A; Université 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., De Kreijger S; Université 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., Sampaio RN; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, 27599-3290, United States., Vincent CA; Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States., Cauët É; Spectroscopy, Quantum Chemistry and Atmospheric Remote Sensing (CP 160/09), Université libre de Bruxelles (ULB), 50 av. F. D. Roosevelt, CP160/09, B-1050 Brussels, Belgium., Jabin I; Laboratoire de Chimie Organique, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium., Tambar UK; Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States., Elias B; Université 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., Troian-Gautier L; Université 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.; Lead contact.
Jazyk: angličtina
Zdroj: Chem catalysis [Chem Catal] 2023 Feb 16; Vol. 3 (2). Date of Electronic Publication: 2023 Jan 04.
DOI: 10.1016/j.checat.2022.100490
Abstrakt: Aryl diazonium salts are ubiquitous building blocks in chemistry, as they are useful radical precursors in organic synthesis as well as for the functionalization of solid materials. They can be reduced electrochemically or through a photo-induced electron transfer reaction. Here we provide a detailed picture of the ground and excited-state reactivity of a series of 9 rare and earth abundant photosensitizers with 13 aryl diazonium salts, which also included 3 macrocyclic calix[4]arene tetradiazonium salts. Nanosecond transient absorption spectroscopy confirmed the occurrence of excited-state electron transfer and was used to quantify cage-escape yields, i.e . the efficiency with which the formed radicals separate and escape the solvent cage. Cage-escape yields were large; increased when the driving force for photo-induced electron transfer increased and also tracked with the C-N 2 + bond cleavage propensity, amongst others. A photo-induced borylation reaction was then investigated with all the photosensitizers and proceeded with yields between 9 and 74%.
Competing Interests: DECLARATION OF INTERESTS The authors declare no competing interests.
Databáze: MEDLINE
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