Abstract: Aryl diazonium salts are ubiquitous building blocks in chem., as they are useful radical precursors in organic synthesis as well as for the functionalization of solid materials. They can be reduced electrochem. 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 nine rare and earth-abundant photosensitizers with 13 aryl diazonium salts, which also included three 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 sep. and escape the solvent cage). Cage-escape yields were large; they increased when the driving force for photo-induced electron transfer increased and also tracked with the C-N+2 bond cleavage propensity, among others. A photo-induced borylation reaction was then investigated with all the photosensitizers and proceeded with yields between 9% and 74%.
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With 1-hydroxy-1,2-benzodioxol-3-(1H)-one; camphor-10-sulfonic acid; [gold(I)Cl(1-(2,4,6-Me3C6H2)-3,5-di(2,6-Me2C6H3) 2-pyridylidene)]; In methanol; chloroform; at 65℃; for 48h;Inert atmosphere; Sealed tube;
General procedure: Triarylpyridylidene-gold complex AuCl(PyC) (6.4 mg, 10 μmol, 5 mol %), heteroarene (0.20 mmol), and aryl(trimethyl)silane (0.20 mmol), 2-iodosobenzoic acids (IBA) (53 mg, 0.20 mmol), (+)-10-camphorsulfonic acid (CSA) (47 mg, 0.20 mmol) and a stirring bar were placed in a screw test tube, and dry chloroform/methanol (1.0 mL/0.10 mL) was added under N2 atmosphere. The tube was sealed with a cap equipped with a Teflon-coated silicon rubber septum, and the mixture was stirred at 65 C for 18-48 h. The reaction was quenched by addition of excess saturated NaHCO3 aq, the aqueous layer was extracted with dichloromethane and the combined organic layers were dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by flash chromatography (FC) to afford the coupling product.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
