A New Rhodium/Copper-Cocatalyzed C–H Oxidation for the Preparation of Isoquinolin-1-ones

Abstract

A new and efficient rhodium/copper-cocatalyzed C–H oxidation reaction of isoquinolinium N-amides has been developed. In the presence of rhodium(II) acetate dimer, copper(II) chloride, a ligand and sodium tert-butoxide, a variety of isoquinolin-1-ones were prepared in moderate to good yields via ortho C–H oxidation.

Key words

rhodium(II) acetate dimer - copper(II) chloride - isoquinolinium N-amides - C–H oxidation - isoquinolin-1-ones

• References

• 1a Wu XF, Neumann H, Beller M. Chem. Rev. 2013; 113: 1
• 1b Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
• 1c Joule JA, Mills K. Heterocyclic Chemistry . 4th ed. Blackwell; Oxford: 2000
• 2a Van HT M, Cho WJ. Bioorg. Med. Chem. Lett. 2009; 19: 2551
• 2b Xie C, Veitch NC, Houghton PJ, Simmonds MS. J. Phytochemistry 2004; 65: 3041
• 2c Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Moritano Y, Saruta K, Higashijima T, Kotera J, Takagi M, Kokkawa K, Omori K. J. Med. Chem. 2001; 44: 2204
• 3 Guastavino JF, Barolo SM, Rossi RA. Eur. J. Org. Chem. 2006; 3898
• 4a Tang QZ, Xia DX, Jin XQ, Zhang Q, Sun XQ, Wang CY. J. Am. Chem. Soc. 2013; 135: 4628
• 4b Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
• 4c Ackermann L. Chem. Rev. 2011; 111: 1315
• 4d C-H Activation . Yu J.-Q, Shi Z. Springer; Berlin: 2010
• 5a Cheng X.-F, Li Y, Su YM, Yin F, Wang J.-Y, Sheng J, Vora HU, Wang X.-S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 1236
• 5b Yao B, Song RJ, Liu Y, Xie Y.-X, Li J.-H, Wang MK, Tang R.-Y, Zhang X.-G, Deng C.-L. Adv. Synth. Catal. 2012; 354: 1890
• 5c Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
• 5d Ding QP, Chen ZY, Yu XX, Peng YY, Wu J. Tetrahedron Lett. 2009; 50: 340
• 5e Peshkov VA, Pereshivko OP, Van Hove S, Ermolat’ev DS, Van der Eycken EV. Synthesis 2011; 3371

For selected papers, see:
• 6a Sharma S, Kim AJ, Park E, Park J, Kim MY, Kwak JH, Lee SH, Jung YH, Kim IS. Adv. Synth. Catal. 2013; 355: 667
• 6b Wu Z.-Q, Luo F.-H, Chen S, Li Z.-K, Xiang H.-F, Zhou X.-G. Chem. Commun. 2013; 49: 7653
• 6c Sharma A, Vacchani D, Eycken EV. Chem. Eur. J. 2013; 19: 1158
• 6d Leow D, Li G, Mei T.-S, Yu J.-Q. Nature 2012; 486: 518
• 6e Zhang X.-G, Dai H.-X, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 11948
• 7 Song G.-Y, Chen D, Pan C.-L, Crabtree RH, Li X.-W. J. Org. Chem. 2010; 75: 7487
• 8 Hyster T, Rovis T. J. Am. Chem. Soc. 2010; 132: 10565
• 9a Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013; 113: 6234
• 9b Zhang H, Zhao L, Wang D.-X, Wang M.-X. Org. Lett. 2013; 15: 3836
• 9c Gallardo-Donaire J, Martin R. J. Am. Chem. Soc. 2013; 135: 9350
• 9d Wang Y.-F, Chen H, Zhu X, Chiba S. J. Am. Chem. Soc. 2012; 134: 11980
• 9e Xu H.-J, Liang Y.-F, Cai Z.-Y, Qi H.-X, Yang C.-Y, Feng Y.-S. J. Org. Chem. 2011; 76: 2296
• 9f Morimoto K, Hirano K, Satoh T, Miura M. Org. Lett. 2010; 12: 2068
• 9g Wei W.-T, Zhou M.-B, Fan J.-H, Liu W, Hu M, Xie P, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 3638
• 10a Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
• 10b Chen Z.-Y, Yu X.-X, Wu J. Chem. Commun. 2010; 46: 6356
• 10c Shan G, Han X.-S, Lin Y, Yu S.-Y, Rao Y. Org. Biomol. Chem. 2013; 11: 2318
• 10d Berman AM, Bergman RG, Ellman JA. J. Org. Chem. 2010; 75: 7863
• 11a Yao B, Deng CL, Liu Y, Tang RY, Zhang XG, Li JH. Chem. Commun. 2015; 51: 4097
• 11b Gao DW, Gu Q, You SL. ACS Catal. 2014; 4: 2741
• 11c Yao B, Song RJ, Liu Y, Xie YX, Li JH, Wang MK, Tang YY, Zhang XG, Deng CL. Adv. Synth. Catal. 2012; 354: 1890
• 11d Pool JA, Scott BL, Kiplinger JL. J. Am. Chem. Soc. 2005; 127: 1338
• 11e Larivee A, Mousseau JJ, Charette AB. J. Am. Chem. Soc. 2008; 130: 52