Isoquinoline N-Oxide Synthesis under Pd-Catalysed C–H Activation/Annulation Processes

Abstract

An oxime directed C–H activation–annulation reaction for the selective synthesis of a range of isoquinoline N-oxides has been developed. Under palladium-catalyzed acid-assisted conditions, the reaction undergoes concerted metallation deprotonation followed by carbopalladation and transmetallation to give poly­substituted isoquinoline N-oxides in moderate to good yields.

Key words

oxime C–H activation–annulation - isoquinoline N-oxide - palladium catalysis

• References


For selected examples, see:
• 1a Wang L, Huang J, Peng S, Liu H, Jiang X, Wang J. Angew. Chem. Int. Ed. 2013; 52: 1768
• 1b Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 2084
• 1c Wang Z.-Q, Liang Y, Lei Y, Zhou M.-B, Li J.-H. Chem. Commun. 2009; 5242
• 1d Elakkar E, Floris B, Galloni P, Tagliatesta P. Eur. J. Org. Chem. 2005; 889

For selected examples, see:
• 2a Zhu C, Falck JR. Org. Lett. 2011; 13: 1214
• 2b McAtee DM. S, Dasgupta S, Watson MP. Org. Lett. 2011; 13: 3490
• 2c Li DD, Yuan TT, Wang GW. Chem. Commun. 2011; 47: 12789
• 2d Wang F, Song GY, Li XW. Org. Lett. 2010; 12: 5430

For selected examples, see:
• 3a Ackermann L, Lygin AV. Org. Lett. 2012; 14: 764
• 3b Porcheddu A, Mura MG, Luca LD, Pizzetti M, Taddei M. Org. Lett. 2012; 14: 6112
• 3c Huestis MP, Chan L, Stuart DR, Fagnou K. Angew. Chem. Int. Ed. 2011; 123: 1374
• 3d Chen JL, Pang QY, Sun YB, Li XW. J. Org. Chem. 2011; 76: 3523
• 3e Wei XH, Zhao M, Du ZY, Li XW. Org. Lett. 2011; 13: 4636
• 3f Zhou F, Han XL, Lu XY. Tetrahedron Lett. 2011; 52: 4681
• 3g Chen JL, Song GY, Pan CL, Li XW. Org. Lett. 2010; 12: 5426
• 3h Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
• 3i Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N. Angew. Chem. Int. Ed. 2009; 48: 4572

For selected examples, see:
• 4a Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142
• 4b Lu S, Lin Y, Zhong H, Zhao K, Huang J. Tetrahedron Lett. 2013; 54: 2001
• 4c Zhang N, Li B, Zhong H, Huang J. Org. Biomol. Chem. 2012; 10: 9429
• 4d Zhong H, Yang D, Wang S, Huang J. Chem. Commun. 2012; 48: 3236
• 4e Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14952
• 4f Ackermann L, Lygin AV, Hofmann N. Angew. Chem. Int. Ed. 2011; 50: 6379
• 4g Song GY, Chen D, Pan CL, Crabtree RH, Li XW. J. Org. Chem. 2010; 75: 7487
• 4h Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
• 4i Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010; 39: 744

For selected examples, see:
• 5a Shi XY, Li CJ. Adv. Synth. Catal. 2012; 354: 2933
• 5b Ackermann L, Pospech J. Org. Lett. 2011; 13: 4153
• 5c Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362

For selected examples, see:
• 6a Kuram MR, Bhanuchandra M, Sahoo AK. Angew. Chem. Int. Ed. 2013; 52: 4607
• 6b Lee DH, Kwon KH, Yi CS. J. Am. Chem. Soc. 2012; 134: 7325
• 6c Kundu D, Samim M, Majee A, Hajra A. Chem. Asian J. 2011; 6: 406

For selected examples, see:
• 7a Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142
• 7b Ackermann L, Pospech J, Graczyk K, Rauch K. Org. Lett. 2012; 14: 930
• 7c Chinnagolla RK, Jeganmohan M. Chem. Commun. 2012; 48: 2030
• 7d Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362
• 7e Ueura K, Satoh T, Miura M. Org. Lett. 2007; 9: 1470
• 8a Yu WY, Sit WN, Zhou Z, Chan AS.-C. Org. Lett. 2009; 11: 3174
• 8b Thirunavukkarasu VS, Parthasarathy K, Cheng C.-H. Angew. Chem. Int. Ed. 2008; 120: 9604
• 9a Zhang XP, Chen D, Zhao M, Zhao J, Jia AQ, Li XW. Adv. Synth. Catal. 2011; 353: 719
• 9b Parthasarathy K, Cheng CH. J. Org. Chem. 2009; 74: 9359
• 10a Chinnagolla RK, Pimparkar S, Jeganmohan M. Org. Lett. 2012; 14: 3032
• 10b Kornhaaß C, Li J, Ackermann L. J. Org. Chem. 2012; 77: 9190
• 11 Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
• 12 Shih WC, Teng CC, Parthasarathy K, Cheng CH. Chem. Asian J. 2012; 7: 306