A mild
and efficient protocol for the intramolecular aromatic C–H
oxygenation of 2-biphenylcarboxylic acids has been achieved via iron
photocatalysis. The 2-biphenylcarboxylic acids with a diverse array
of substituents at both phenyl rings could furnish the oxygenation
products in good to excellent yields. We speculate that the aryl carboxylate–iron(III)
complexes should generate the aroyloxy radicals and iron(II) upon
visible light irradiation.
A mild and practical C(sp 3 )−H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2alkylbenzoic acid substrate, magnesium ion, and bromate anion.
A practical nickel-catalyzed C−N cross-coupling reaction between diarylamines and aryl halides has been developed using commercially available NiCl 2 (dppf) as the catalyst. This robust method can be efficiently applied to a variety of diarylamines which are privileged motifs in materials science, including phenoxazines, phenothiazines, carbazoles, diphenylamines, 9-10dihydroacridines, 10,11-dihydro-5H-dibenzo[b,f ]azepines, 5H-dibenzo[b,f ]azepines, and 9H-tribenzo[b,d,f ]azepines.
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