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- W3140654315 abstract "Transition metal-catalyzed direct C-H bond functionalization has been used in the construction of a variety of carbon-carbon and carbon-heteroatom bonds with features of step-economics and green chemistry primarily. By this strategy, a series of valuable polyfunctional compounds can be synthesized expediently. The efficient coordination of nitroso to transition metals made this group act as a favorable directing group to carry out the functionalization of inert C-H bond. N-Nitrosoanilines are also a class of very useful medicinal compounds and synthetic materials for the preparation of various nitrogen-containing compounds. In this paper, an efficient and highly regioselective direct ortho-acyloxylation of N-alkyl-N-nitrosoarylamines was developed. Under the catalysis of palladium, by the use of HOAc/Ac2 O mixture as the Ac O-source and solvent, and Ph I(OAc)2 as the oxidant, the reaction gave acyloxylation products on ortho-position of N-alkyl-N-nitrosoarylamines with very high selectivity in moderate to good yields. The reaction conditions were optimized to be N-alkyl-N-nitrosoarylamines mixed with Pd(OAc)2(10 mol%), and Ph I(OAc)2 in HOAc/Ac2O(1:1, v/v), under an air atmosphere at 70°C for 6 h. The reaction can tolerate a series of functional groups such as alkyl, alkoxyl, halogen and ester, etc. The mechanism for the reaction was proposed to be via a five-membered cyclopalladated intermediate which was formed by the coordination of nitroso to palladium, and a Pd(II)/Pd(IV) catalytic cycle was suggested in this transformation. The reaction could proceed under relatively mild reaction conditions, making the method highly applicable." @default.
- W3140654315 created "2021-04-13" @default.
- W3140654315 creator A5014315118 @default.
- W3140654315 date "2015-01-01" @default.
- W3140654315 modified "2023-09-27" @default.
- W3140654315 title "Palladium-catalyzed N-nitroso-directed ortho C(sp~2)-H acyloxylation of N-alkyl-N-nitrosoarylamines" @default.
- W3140654315 hasPublicationYear "2015" @default.
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