Synlett, Table of Contents Synlett 2015; 26(14): 2033-2036DOI: 10.1055/s-0034-1380440 letter © Georg Thieme Verlag Stuttgart · New YorkPalladium(II)-Catalyzed C–H Acylation with Arylglycine Derivatives Weizheng Fan School of Pharmaceutical Science, Jiangnan University, Wuxi 214122, P. R. of China Email: fengbainian@jiangnan.edu.cn , Jiapeng Su School of Pharmaceutical Science, Jiangnan University, Wuxi 214122, P. R. of China Email: fengbainian@jiangnan.edu.cn , Bainian Feng* School of Pharmaceutical Science, Jiangnan University, Wuxi 214122, P. R. of China Email: fengbainian@jiangnan.edu.cn› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A novel palladium(II)-catalyzed ortho acylation of arenes with arylglycines in the presence of Cu(OAc)2 and K2S2O8 to afford the benzophenones was developed. This direct C–H acylation is suitable for a broad range of substrates. The control experiments suggested a possible oxidative addition mechanism. Key words Key wordspalladium(II)-catalyzed - ortho acylation - arylglycine - C–H activation - oxidative addition Full Text References References and Notes For recent reviews, see: 1a Mousseau JJ, Charette AB. Acc. Chem. Res. 2013; 46: 412 1b Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236 1c Bras JL, Muzart J. Chem. Rev. 2011; 111: 1170 1d McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885 1e Baudoin O. Chem. Soc. Rev. 2011; 40: 4902 1f Wencel-Delord J, Dröge T, Kiu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740 1g Ackermann L. Chem. Rev. 2011; 111: 1315 1h Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068 1i Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147 1j Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624 1k Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094 1l Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949 1m Kakiuchi F, Kochi T. 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Ed. 2009; 48: 9412 18 Synthesis of 3a–v A mixture of 1 (0.5 mmol), 2 (0.6 mmol), DMSO (5% H2O aq, 5 mL), Pd(OAc)2 (5 mol%), Cu(OAc)2 (10 mol%), and K2S2O8 (2 equiv) was stirred at 120 °C under Ar atmosphere for 24 h. The reaction mixture was washed with H2O, and the aqueous phase was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to give the corresponding products (3a–d,7b 3f–k,7b 3n–s 7b). Compound 3e: yield 15%, white solid. 1H NMR (500 MHz, CDCl3): δ = 8.32 (d, J = 4.6 Hz, 1 H), 7.68 (m, 2 H), 7.52 (m, 2 H), 7.50 (m, 1 H), 7.41 (t, J = 7.2 Hz, 1 H), 7.25 (m, 2 H), 7.18 (m, 2 H), 7.0 (m, 1 H), 1.13 (s, 9 H). 13C NMR (125 MHz, CDCl3): δ = 197.2, 158.0, 155.2, 148.5, 140.2, 136.8, 135.9, 131.5, 129.9, 129.3, 128.4, 127.8, 126,9, 121.3, 119.5, 114.1, 34.5, 15.8. HRMS: m/z calcd for C22H21NO: 315.1623; found: 315.1626. 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