Iodine-Catalyzed C–N Cleavage of Tertiary Amines: Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds

Abstract

A novel and efficient iodine-catalyzed C–N cleavage of tertiary amines via an sp³ C–H bond oxidative coupling reaction is described. A wide range of methylene-bridged bis-1,3-dicarbonyl compounds were synthesized in up to 92% yield by using an environmentally benign catalytic system in combination with 1,3-dicarbonyl compounds.

Key words

iodine - oxidative coupling - C–N cleavage - tertiary amines - methylene-bridged bis-1,3-dicarbonyl compounds

• References

• 1a Alston TA, Porter DJ. T, Bright HJ. Acc. Chem. Res. 1983; 16: 418
• 1b Roglans A, Pla-Quintana A, Moreno-Mañas M. Chem. Rev. 2006; 106: 4622
• 1c Ueno S, Chatani N, Kakiuchi F. J. Am. Chem. Soc. 2007; 129: 6098
• 2a Akiyama F, Miyazaki H, Kaneda K, Teranishi S, Fujiwara Y, Abe M, Taniguchi H. J. Org. Chem. 1980; 45: 2359
• 2b Laine RM, Thomas DW, Cary LW. J. Am. Chem. Soc. 1982; 104: 1763
• 2c Wenkert E, Han A.-L, Jenny C.-J. J. Chem. Soc., Chem. Commun. 1988; 975
• 3a Cameron TM, Abboud KA, Boncella JM. Chem. Commun. 2001; 1224
• 3b Blakey SB, MacMillan DW. C. J. Am. Chem. Soc. 2003; 125: 6046
• 3c Caddick S, Cloke FG. N, Hitchcock PB, deKLewis AK. Angew. Chem. Int. Ed. 2004; 43: 5824
• 3d Takano K, Inagaki A, Akita M. Chem. Lett. 2006; 35: 434
• 3e Kuninobu Y, Nishi M, Takai K. Chem. Commun. 2010; 46: 8860
• 3f Burling S, Mahon MF, Powell RE, Whittlesey MK, Williams JM. J. J. Am. Chem. Soc. 2006; 128: 13702
• 3g Häller LJ. L, Page MJ, Erhardt S, Macgregor SA, Mahon MF, Abu Naser M, Vélez A, Whittlesey MK. J. Am. Chem. Soc. 2010; 132: 18408
• 3h Bonnano JB, Henry TP, Neithamer DR, Wolczanski PT, Lobkovsky EB. J. Am. Chem. Soc. 1996; 118: 5132
• 4a Felpin FX, Nassar-Hardy L, Callonnec FL, Fouquet E. Tetrahedron 2011; 67: 2815
• 4b Taylor JG, Moro AV, Correia CR. D. Eur. J. Org. Chem. 2011; 1403
• 5a Hoerter JM, Otte KM, Gellman SH, Cui Q, Stahl SS. J. Am. Chem. Soc. 2008; 130: 647
• 5b Liu C.-R, Li M.-B, Cheng D.-J, Yang C.-F, Tian S.-K. Org. Lett. 2009; 11: 2543
• 5c Zhu M.-K, Zhao J.-F, Loh T.-P. Org. Lett. 2011; 13: 6308
• 6a Wang A, Jiang H, Li X. J. Org. Chem. 2011; 76: 6958
• 6b Zhao X, Liu D, Guo H, Liu Y, Zhang W. J. Am. Chem. Soc. 2011; 133: 19354
• 6c Li B.-J, Wang H.-Y, Zhu Q.-L, Shi Z.-J. Angew. Chem. Int. Ed. 2012; 51: 3948
• 6d Li M.-B, Wang Y, Tian S.-K. Angew. Chem. Int. Ed. 2012; 51: 2968
• 6e Krackl S, Someya CI, Enthaler S. Chem. Eur. J. 2012; 18: 15267
• 6f Wang Y, Chi Y, Zhang W.-X, Xi Z. J. Am. Chem. Soc. 2012; 134: 2926
• 6g Huang H, Ji X, Wu W, Huang L, Jiang H. J. Org. Chem. 2013; 78: 3774
• 6h Liang D, He Y, Liu L, Zhu Q. Org. Lett. 2013; 15: 3476
• 6i Li Y, Guo F, Zha Z, Wan Z. Chem. Asian J. 2013; 8: 534
• 6j Szostak M, Spain M, Procter DJ. Angew. Chem. Int. Ed. 2013; 52: 7237
• 6k Xiang L, Mashima K, Xie Z. Chem. Commun. 2013; 49: 9039
• 6l Hao Q, Miao T, Zhang X. Org. Biomol. Chem. 2013; 11: 1867
• 6m Zhang J, Yi W, Chen Z, Zhou X. Dalton Trans. 2013; 42: 5826
• 6n Xie J, Xue Q, Jin H, Li H, Cheng Y, Zhu C. Chem. Sci. 2013; 4: 1281
• 7a Li H, He Z, Guo X, Li W, Zhao X, Li Z. Org. Lett. 2009; 11: 4176
• 7b Liu W, Liu JD, Nishihara OY, Guo X, Li Z. Org. Lett. 2011; 13: 6272
• 8a Zhang L, Peng C, Zhao D, Wang Y, Fu H.-J, Shen Q, Li J.-X. Chem. Commun. 2012; 48: 5928
• 8b Chen J, Liu B, Liu D, Liu S, Cheng J. Adv. Synth. Catal. 2012; 354: 2438
• 8c Zhao D, Wang Y, Zhu M.-X, Shen Q, Zhang L, Du Y, Li J.-X. RSC Adv. 2013; 3: 10272
• 9 Balamurugan R, Manojveer S. Chem. Commun. 2011; 47: 11143
• 10 Wu W, Su W. J. Am. Chem. Soc. 2011; 133: 11924
• 11a Liu Y, Yao B, Deng C.-L, Tang R.-Y, Zhang X.-G, Li J.-H. Org. Lett. 2011; 13: 2184
• 11b Tang R.-Y, Guo X.-K, Xiang J.-N, Li J.-H. J. Org. Chem. 2013; 78: 11163
• 12 Li L.-T, Huang J, Li H.-Y, Wen L.-J, Wang P, Wang B. Chem. Commun. 2012; 48: 5187
• 13a Hon Y.-S, Hsu T.-R, Chen C.-Y, Lin Y.-H, Chang F.-J, Hsieh C.-H, Szu P.-H. Tetrahedron 2003; 59: 1509
• 13b Tan J.-N, Li H, Gu Y. Green Chem. 2010; 12: 1772
• 13c Gu Y, De Sousa R, Frapper G, Bachmann C, Barrault J, Jérôme F. Green Chem. 2009; 11: 1968
• 14a Guo S, Chan B, Xie Y, Xia C, Huang H. Org. Lett. 2011; 13: 522
• 14b Xie Y, Hu J, Wang Y, Xia C, Huang H. J. Am. Chem. Soc. 2012; 134: 20613
• 15 Zhang X, Yang W, Wang L. Org. Biomol. Chem. 2013; 11: 3649
• 16 Shen H, Lu X, Jiang K.-Z, Yang K.-F, Lu Y, Zheng Z.-J, Lai G.-Q, Xu L.-W. Tetrahedron 2012; 68: 8916
• 17a Finkbeiner P, Nachtsheim BJ. Synthesis 2013; 45: 979
• 17b Figueiredo CA. M, Reddy KR. K. K, Monteiro PA, de Carvalho JE, Ruiz AL. T. G, Silva LF. Synthesis 2013; 45: 1076
• 17c Jereb M, Vražič D, Zupan M. Tetrahedron 2011; 67: 1355
• 17d Zhu Y.-P, Liu M, Jia F, Yuan J, Gao Q, Lian M, Wu A. Org. Lett. 2012; 14: 3392
• 17e Sobhani S, Jahanshahi R. Synth. Commun. 2013; 43: 3247
• 17f Jia Z, Nagano T, Li X. Eur. J. Org. Chem. 2013; 858
• 17g Nobuta T, Tada N, Fujiya A, Kariya A, Miura T, Itoh A. Org. Lett. 2013; 15: 574
• 17h Ge W, Zhu X, Wei Y. RSC Adv. 2013; 3: 10817
• 17i Bedrac L, Iskra J. Adv. Synth. Catal. 2013; 355: 1243
• 17j Gao L, Xiong S, Wan C. Synlett 2013; 24: 1322
• 17k Jia F.-C, Zhu Y.-P, Liu M.-C. Tetrahedron 2013; 69: 7038
• 17l Lao Z.-Q, Zhong W.-H, Lou Q.-H, Li Z.-J, Meng X.-B. Org. Biomol. Chem. 2012; 10: 7869
• 17m Li L.-T, Huang J, Li H.-Y, Wen L.-J, Wang P, Wang B. Chem. Commun. 2012; 48: 5187
• 17n Wei W, Zhang C, Xu Y, Wan X. Chem. Commun. 2011; 47: 10827
• 17o Lamani M, Prabhu KR. J. Org. Chem. 2011; 76: 7938
• 17p Wu W.-B, Huang J.-M. Org. Lett. 2012; 14: 5832
• 18a Nobuta T, Fujiya A, Yamaguchi T, Tada N, Miura T, Itoh A. RSC Adv. 2013; 3: 10189
• 18b Dhineshkumar J, Lamani M, Alagiri K, Prabhu K. Org. Lett. 2013; 15: 1092
• 19 Yan Y, Wang Z. Chem. Commun. 2011; 47: 9513