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• W2045794098 endingPage "3595" @default.
• W2045794098 startingPage "3587" @default.
• W2045794098 abstract "The palladated primary amines [Pd{C6H3CH2NH2-2-X-5}(μ-Br)]2 [X = H (1a), OMe (1b), NO2 (1c), F (1d)] react with isocyanides (Pd:RNC = 1:1) to give [Pd{C6H3CH2NH2-2-X-5}Br(RNC)] [R = Xy = C6H3Me2-2,6, X = H (2a), OMe (2b), NO2 (2c), F (2d), R = tBu, X = H (3a), OMe (3b), NO2 (3c), F (3d)]. When XyNC reacts with 1a (Pd:RNC = 1:2) or with 2a (Pd:RNC = 1:1), the complex [Pd{(CNXy)C6H4CH2NH2-2}(XyNC)Br] (4a) is obtained. The reactions of complexes 1 with isocyanides in the ratio Pd:RNC = 1:3 lead to Pd(I) complexes [Pd2Br2L4] [L = XyNC (5); L = tBu (6)]. On the basis of NMR data we propose the following reaction pathway for this reduction process: (1) formation of the corresponding monomer 2 or 3, (2) insertion of one molecule of the isocyanide into the Pd−C bond of 2 or 3 to give [Pd{(CNR)C6H3CH2NH2-2-X-5}(RNC)Br], (3) cleavage of the N−Pd bond and coordination of a new isocyanide molecule to give complexes [Pd{(CNR)C6H3CH2NH2-2-X-5}(RNC)2Br] [detected in solution for R = Xy, X = H (7a) and isolated as an acetylated derivative of this complex [Pd{(CNXy)C6H4CH2NHC(O)Me-2}(XyNC)2Br] (8a)], and (4) decomposition of these complexes to give 5 or 6. The organic product of these reactions was not identified. By refluxing mixtures of complexes 1 with RNC and TlOTf (Pd:RNC:TfO = 1:1:1) the corresponding isoindolinium triflates 9·OTf [R = Xy, X = H (9a·OTf), OMe (9b·OTf), F (9d·OTf)] or 10·OTf [R = tBu, X = H (10a·OTf), OMe (10b·OTf), F (10d·OTf)] were isolated and characterized. A mechanism of formation of these isoindolinium triflates is proposed. When the reaction between 1a and XyNC (Pd:RNC = 1:1) was carried out in refluxing toluene in the absence of TlOTf, or when 2a was refluxed in toluene, an insertion of the isocyanide occurs in both cases to give [Pd{(CNXy)C6H4CH2NH2-2}Br]2 (11). If 1a or 2a is reacted with XyNC (Pd:RNC = 1:1.25 or 1:0.25, respectively), the complex [PdBr2{2-(XyNH)-isoindole}2] (12) is formed. A proposal for the reaction pathway of this process is discussed. The crystal structures of 3d, 9a·OTf, and 12 have been determined." @default.
• W2045794098 created "2016-06-24" @default.
• W2045794098 creator A5021926139 @default.
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• W2045794098 date "2002-07-23" @default.
• W2045794098 modified "2023-10-16" @default.
• W2045794098 title "Palladium-Assisted Formation of Carbon−Carbon Bonds. Part 10.¹ Insertion Reactions of Isocyanides into the Pd−C Bond of Orthopalladated Primary Amines. Synthesis of 2-R-Aminoisoindolinium Salts (R = ^tBu, 2,6-Xylyl)" @default.
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• W2045794098 doi "https://doi.org/10.1021/om020365n" @default.
• W2045794098 hasPublicationYear "2002" @default.
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