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%.
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2-(((4-cyclohexylphenyl)amino)methyl)-5-iodophenol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
General procedure: Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82%) E6 as white solid.
Chemistry
Pharmaceutical Intermediates
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Material Science
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120K+ Compounds
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