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• W2023751303 abstract "The reactions of 1 and 2 towards Ph 2 PH and Ph 2 PLi, studied to synthesize the novel P,N ligands 3a,b in comparison with 6 , display different selectivity for the main products, C-H and C-C versus C-P coupling. The background of higher air sensitivity of 3a,b compared to 6 , preliminary studies of a Pd/ 6 catalyzed C-N coupling and crystal structures are reported. The synthesis of quinoxaline P,N ligands by monoamination of 2,3-dichloroquinoxaline ( 1 ) to 2-amino-3-chloroquinoxalines 2a , b and the subsequent substitution of chlorine by a diphenylphosphanyl group was studied. Whereas the reaction of 2a , b with Ph 2 PH in the presence (or absence) of catalytic amounts of palladium acetate furnished only minor amounts of the expected ligands in favor of tetraphenyldiphosphane and dechlorinated quinoxalines, the coupling with Ph 2 PLi in ether provided the novel NH-functional P,N hybrid ligands 3a , b with a quinoxaline scaffold in moderate to good yields. 3a is slightly and 3b somewhat more sensitive to air oxidation, leading to the P-oxides 4a , b . The more reactive 1 forms with Ph 2 PH only a small amount of 2-chloro-3-diphenylphosphanylquinoxaline 5 and traces of the quinoxaline-bis(phosphane) 6 . The main products are 2,2′-bis(quinoxaline) and Ph 2 PCl, which converts residual Ph 2 PH into tetraphenyldiphosphane. The coupling with Ph 2 PLi in diethyl ether, however, gave in a fast reaction high yields of 6 , exceeding those of 3a , b , with interfering NH functions. Semi-empirical quantum chemical calculations (PM6) illuminate the background of the air sensitivity of 3a , b , whereas the recently reported 6 is air stable. Preliminary studies for use of the ligands in catalysis with the air-stable 6 , showed moderate to good yields in the Pd-catalyzed C–N cross coupling of 2-bromopyridine with mesityl amine. Complex formation was confirmed by isolation of the Pd complex 7 . The structure elucidation of the new compounds is based on conclusive NMR data and crystal structure analyses for 2b , 3a , 4a and 4b ." @default.
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• W2023751303 date "2013-02-01" @default.
• W2023751303 modified "2023-10-18" @default.
• W2023751303 title "Comparison of the reactivity of 2-amino-3-chloro- and 2,3-dichloroquinoxalines towards Ph2PH and Ph2PLi and of the properties of diphenylphosphanyl-quinoxaline P,N and P,P ligands" @default.
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• W2023751303 doi "https://doi.org/10.1016/j.poly.2012.08.089" @default.
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