Palladium-catalyzed aromatic

Jiang L, Buchwald SL (2004) Palladium-catalyzed aromatic carbon-nitrogen bond formation. In de Meijere A, Diedeiich F (eds) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley-VCH, Weinheim... 

Scheme 11.10. Copper- and Palladium-Catalyzed Aromatic Substitution...

Palladium-catalyzed aromatic C—O bond formation is less developed than palladium-catalyzed aryl amination. Except when the aryl halide is strongly electron deficient,107-110 catalysts ligated by the conventional aryl phosphines such as DPPF and BINAP are ineffective for coupling of... 

A method for the monoarylation of (15,25)-l,2-diaminocyclo-hexane by means of palladium-catalyzed aromatic amination has been recently described (eq 13). The resulting new ligands were tested in the catalytic asymmetric transfer hydrogenation of acetophenone. 

Manger CC, Mignani G. Synthetic applications of Buchwald s phosphines in palladium-catalyzed aromatic-bond-forming reactions. Aldrichimica Acta 2006 39 17-24. 

Kosugi, M., Kameyama, M., Migita, T. Palladium-catalyzed aromatic amination of aryl bromides with N,N-diethylaminotributyltin. Chem. 

Guram, A. S., Buchwald, S. L. Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes. J. Am. Chem. See. 1994, 116,7901-7902. 

Lin and Tao used P(Z-Bu)3 for the synthesis of benzo[a]aceanthranylene core compounds (acen) 98. Pure red-emitting devices were fabricated using acen as both holetransporting and emitting materials [157]. Palladium-catalyzed aromatic C—N coupling reactions and cyclization were carried out in one pot in the presence of Pd(OAc)2 and r-Bu3P [157]. 

Li B-J, Yang S-D, Shi Z-J (2008) Recent advances in direct arylation via Palladium-catalyzed aromatic C-H activation. Synlett 949-957... 

Gorelsky, S.I., Lapointe, D., Fagnou, K., 2012. Analysis of the palladium-catalyzed (aromatic) C—H bond metalation-deprotonation mechanism spanning the entire spectrum of arenes. I. Org. Chem. 77, 658-668. 

Palladium-catalyzed aromatic amination of aryl halides, developed independently by Buchwald and Hartwig, is a useful tool for the construction of C—N bonds. Caravieilhes and coworkers examined this aromatic amination using a microreactor [16]. When the reaction of p-bromotoluene and piperidine with Pd(OAc)2/ biarylphosphine as a catalyst system and sodium tert-pentoxide as a base in xylene was carried out using a CPC CYTOS Lab System, the desired coupling product was obtained in quantitative yield with a 7.5 min residence time (Scheme 6.5). 

G. Mignani, Successfid application of microstructured continuous reactor in the palladium catalyzed aromatic amination,/. Organomet. Chem. 2005, 690, 3627-3629. 

Palladium-catalyzed aromatic C-H acetoxylation was first reported in 1966 [100, 101]. In 1971, Henry proposed Pd(IV) intermediates in the Pd-catalyzed acetoxylation of benzene with K2Cr207 in AcOH [102], Subsequent reports by Stock [103] and Crabtree [104] also discussed the possible intermediacy of Pd(IV) complexes in the acetoxylation of benzene (Fig. 27a). In 2004, Sanford reported the regioselec-tive ort/to-acetoxylation of 2-arylpyridines and proposed a reaction mechanism involving aromatic C-H metallation at Pd(II), oxidation of the resulting aryl Pd(II) intermediate to a Pd(IV) complex, and product-forming C-O reductive elimination (Fig. 27b) [105-108]. 

Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation... 

I 13 Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation Pd(OAc)2 (1 mol%)... 

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