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2.11.4 Conclusions

DOI: 10.1055/sos-SD-218-00206

Li, D.-D.; Wang, G.-W.Science of Synthesis: Catalytic Transformations via C—H Activation, (20152400.

Significant advances have been made in palladium-, copper-, and ruthenium-catalyzed arene C—O bond formation via C—H bond activation in recent years. A directing group is usually required to achieve high regioselectivity. Various functional groups, such as amide (anilide/benzamide/Weinreb amide), imine, oxime ether, sulfoximine, azo, pyrrolidinone, carbamate, trifluoromethanesulfonamide, ketone, ester, nitrile, aliphatic alcohol, phenol, silanol, phosphine oxide, carboxylic acid, sulfonic acid, phosphonic and phosphinic acids, as well as hetaryl moieties such as pyridine, pyrimidine, pyrazine, pyrazole, dihydroisoxazole, isoxazole, triazole, benzimidazole, benzoxazole, benzothiazole, benzotriazine, quinoxaline, and quinazolinone, have been fruitfully employed as the directing groups. Acyloxylation, alkoxylation, hydroxylation, and intramolecular C—O cyclization affording dihydrobenzo[b]furans, dibenzofurans, benzofuran[b]ones, biaryl lactones, 2-arylbenzoxazoles, oxasilacycles, aromatic sultones, and benzoxaphosphole 1- and 2-oxides have been successfully realized by palladium-, copper-, and ruthenium-catalyzed arene C—H activation. These transition-metal-catalyzed C—H/C—O processes can be efficiently achieved by utilizing either a monodentate or bidentate directing group. It is anticipated that these developed and to-be-developed methodologies will continue to contribute to the synthesis of many novel organic compounds including bioactive natural products.


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