Direct Access to Isoindolinone Derivatives by Palladium-Catalyzed C–H Activation and Isocyanide Insertion by Using Molecular Oxygen as the Sole Oxidant

Abstract

We report a straightforward, aerobic, palladium-catalyzed C–H activation, followed by isocyanide insertion to synthesize isoindolinone derivatives. This transformation is an efficient and step-economic strategy using oxygen as the sole oxidant. We anticipate that this work will inspire in-depth studies as well as versatile applications in various related fields.

Key words

palladium-catalyzed - C–H activation - isocyanide insertion - isoindolinone - oxygen - heterocycles

• References

• 1 These authors contributed equally to this work.
• 2a Chen X, Engle KM, Wang D.-HYu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
• 2b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 2c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
• 3 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
• 4a Vlaar T, Maes BU. W, Ruijter E, Orru RV. A. Angew. Chem. Int. Ed. 2013; 52: 7084
• 4b Lang S. Chem. Soc. Rev. 2013; 42: 4867
• 4c Qiu G, Ding Q, Wu J. Chem. Soc. Rev. 2013; 42: 5257
• 5 Curran DP, Du W. Org. Lett. 2002; 4: 3215
• 6 Tobisu M, Imoto S, Ito S, Chatani N. J. Org. Chem. 2010; 75: 4835
• 7 Wang Y, Wang H, Peng J, Zhu Q. Org. Lett. 2011; 13: 4604
• 8 Wang Y, Zhu Q. Adv. Synth. Catal. 2012; 354: 1902
• 9 Peng J, Liu L, Hu Z, Huang J, Zhu Q. Chem. Commun. 2012; 48: 3772
• 10 Hu Z, Liang D, Zhao J, Huang J, Zhu Q. Chem. Commun. 2012; 48: 7371
• 11 Peng J, Zhao J, Hu Z, Liang D, Huang J, Zhu Q. Org. Lett. 2012; 14: 4966
• 12 Xu S, Huang X, Hong X, Xu B. Org. Lett. 2012; 14: 4614
• 13a Chen M, He M, Zhou X, Huang L, Ruan Y, Huang P. Tetrahedron 2005; 61: 1335
• 13b Stuk TL, Assink BK, Bates RC, Erdman DT, Fedij V, Jennings SM, Lassig JA, Smith RJ, Smith TL. Org. Process Res. Dev. 2003; 7: 851
• 13c Belliotti TR, Brink WA, Kesten SR, Rubin JR, Wustrow DJ, Zoski KT, Whetzel SZ, Corbin AE, Pugsley TA, Heffner TG, Wise LD. Bioorg. Med. Chem. Lett. 1998; 8: 1499
• 14 Tyagi V, Khan S, Chauhan PM. S. Synlett 2013; 24: 645
• 15 Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
• 16 Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 3066