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Synlett 2014; 25(11): 1621-1625
DOI: 10.1055/s-0033-1341279
DOI: 10.1055/s-0033-1341279
letter
Nickel-Catalyzed sp3 C–H Bond Activation from Decarboxylative CrossCoupling of α,β-Unsaturated Carboxylic Acids with Amides
Further Information
Publication History
Received: 10 March 2014
Accepted after revision: 07 April 2014
Publication Date:
14 May 2014 (online)
Abstract
Nickel-catalyzed functionalization of C(sp3)–H bonds adjacent to a nitrogen atom in amides through decarboxylative cross-coupling of α,β-unsaturated carboxylic acids is reported. A possible reaction mechanism is proposed that involves radical intermediate species.
Primary Data
- for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083 and can be cited using the following DOI: 10.4125/pd0058th.
- Primary Data
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References and Notes
- 1a Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
- 1b Ritleng V, Sirlin C, Pfeffer M. Chem. Rev. 2002; 102: 1731
- 1c Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2006; 45: 1683
- 2a Chatani N, Asaumi T, Ikeda T, Yorimitsu S, Ishii Y, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2000; 122: 12882
- 2b Chatani N, Asaumi T, Yorimitsu S, Ikeda T, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2001; 123: 10935
- 3a Dangel BD, Johnson JA, Sames D. J. Am. Chem. Soc. 2001; 123: 8149
- 3b Sezen B, Franz R, Sames D. J. Am. Chem. Soc. 2002; 124: 13372
- 3c DeBoef B, Pastine SJ, Sames D. J. Am. Chem. Soc. 2004; 126: 6556
- 3d Sezen B, Sames D. J. Am. Chem. Soc. 2005; 127: 5284
- 4a Zhang Y.-H, Li C.-J. Angew. Chem. Int. Ed. 2006; 45: 1949
- 4b Li Z.-P, Yu R, Li H.-J. Angew. Chem. Int. Ed. 2008; 47: 7497
- 4c Suematsu H, Katsuki T. J. Am. Chem. Soc. 2009; 131: 14218
- 4d Richter H, Mancheño OG. Eur. J. Org. Chem. 2010; 4460
- 5a Tsuchikama K, Kasagawa M, Endo K, Shibata T. Org. Lett. 2009; 11: 1821
- 5b Chu L.-L, Zhang X.-G, Qing F.-L. Org. Lett. 2009; 11: 2197
- 6a Evans DA, Morrissey MM, Dorow RL. J. Am. Chem. Soc. 1985; 107: 4348
- 6b Behenna DC, Stoltz BM. J. Am. Chem. Soc. 2004; 126: 15044
- 6c Burger EC, Tunge JA. Org. Lett. 2004; 6: 4113
- 6d Trost BM, Xu J. J. Am. Chem. Soc. 2005; 127: 2846
- 6e Gooßen LJ, Rudolphi F, Oppel C, Rodríguez N. Angew. Chem. Int. Ed. 2008; 47: 3043
- 6f Shang R, Fu Y, Li J.-B, Zhang S.-L, Guo Q.-X, Liu L. J. Am. Chem. Soc. 2009; 131: 5738
- 6g Zhang W.-W, Zhang X.-G, Li J.-H. J. Org. Chem. 2010; 75: 5259
- 7a Tanaka D, Romeril SP, Myers AG. J. Am. Chem. Soc. 2005; 127: 10323
- 7b You S.-L, Dai L.-X. Angew. Chem. 2006; 118: 5372
- 7c Lalic G, Aloise AD, Shair MD. J. Am. Chem. Soc. 2003; 125: 2852
- 7d Lou S, Westbrook JA, Schaus SE. J. Am. Chem. Soc. 2004; 126: 11440
- 8a Yang Y.-Z, Cheng K, Zhang Y.-H. Org. Lett. 2009; 11: 5606
- 8b Wei Y, Kan J, Wang M, Su W.-P, Hong M.-C. Org. Lett. 2009; 11: 3346
- 8c Zhang X.-G, Fan S.-L, He C.-Y, Wan X.-L, Min Q.-Q, Yang J, Jiang Z.-X. J. Am. Chem. Soc. 2010; 132: 4506
- 8d Gandeepan P, Parthasarathy K, Cheng C.-H. J. Am. Chem. Soc. 2010; 132: 8569
- 8e Yamashita M, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 2337
- 8f Fukutani T, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 5198
- 8g Matsushita M, Kamata K, Yamaguchi K, Mizuno N. J. Am. Chem. Soc. 2005; 127: 6632
- 8h Deng G.-J, Zhao L, Li C.-J. Angew. Chem. Int. Ed. 2008; 47: 6278
- 9a Gao YX, Wang G, Chen L, Xu PX, Zhao YF, Zhou YB, Han L.-B. J. Am. Chem. Soc. 2009; 131: 7956
- 9b Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2009; 131: 17052
- 9c Monguchi D, Fujiwara T, Furukawa H, Mori A. Org. Lett. 2009; 11: 1607
- 9d Wang Q, Schreiber SL. Org. Lett. 2009; 11: 5178
- 9e Cheng K, Huang LH, Zhang YH. Org. Lett. 2009; 11: 2908
- 9f Huang LH, Cheng K, Yao BB, Zhao JL, Zhang YH. Synthesis 2009; 3504
- 9g Sun HY, Zhang YH, Guo FF, Zha ZG, Wang ZY. J. Org. Chem. 2012; 77: 3563
- 10a Li Z, Cao L, Li C.-J. Angew. Chem. Int. Ed. 2007; 46: 6505
- 10b Guo X.-W, Yu R, Li H.-J, Li Z. J. Am. Chem. Soc. 2009; 131: 17387
- 10c Volla CM. R, Vogel P. Org. Lett. 2009; 11: 1701
- 10d Ohta M, Quick MP, Yamaguchi J, Wünsch B, Itami K. Chem. Asian J. 2009; 4: 1416
- 11a Montgomery J. Angew. Chem. Int. Ed. 2004; 43: 3890
- 11b Yin W.-Y, He C, Chen M, Zhang H, Lei A.-W. Org. Lett. 2009; 11: 709
- 11c Hachiya H, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2010; 49: 2202
- 11d Oertel AM, Ritleng V, Chetcuti MJ, Veiros LF. J. Am. Chem. Soc. 2010; 132: 13588
- 11e Liu D, Liu C, Li H, Lei A.-W. Angew. Chem. Int. Ed. 2013; 52: 4453
- 12a Tang R.-Y, Xie Y.-X, Xie Y.-L, Xiang J.-N, Li J.-H. Chem. Commun. 2011; 47: 12867
- 12b Shepherd NE, Tanabe H, Xu Y.-J, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 3666
- 12c Mitchell EA, Peschiulli A, Lefevre N, Meerpoel L, Maes BU. W. Chem. Eur. J. 2012; 18: 10092
- 12d Dai C.-H, Meschini F, Narayanam JM. R, Stephenson CR. J. J. Org. Chem. 2012; 77: 4425
- 12e Li G.-C, Qian S.-Y, Wang C.-X, You J.-S. Angew. Chem. Int. Ed. 2013; 52: 7837
- 13a Li H.-M, Xie J, Xue Q.-C, Cheng Y.-X, Zhu C.-J. Tetrahedron Lett. 2012; 53: 6479
- 13b Xu K, Hu Y.-B, Zhang S, Zha Z.-G, Wang Z.-Y. Chem. Eur. J. 2012; 18: 9793
- 13c Wang G, Yu Q.-Y, Chen S.-Y, Yu X.-Q. Org. Biomol. Chem. 2014; 12: 414
- 14a Deng S.-J, Taunton J. J. Am. Chem. Soc. 2002; 124: 916
- 14b Ohnishi Y, Sakai M, Nakao S, Kitagawa O. Org. Lett. 2011; 13: 2840
- 15a Li X.-B, Curran DP. Org. Lett. 2010; 12: 612
- 15b Hu DX, Grice P, Ley SV. J. Org. Chem. 2012; 77: 5198
- 16a Zhao LX, Shang XJ, Cui ZL, Liu ZQ. Org. Lett. 2012; 14: 3219
- 16b Cui ZL, Shang XJ, Shao XF, Liu ZQ. Chem. Sci. 2012; 3: 2853
- 17 Russell GA, Ngoviwatchai P. J. Org. Chem. 1989; 54: 1836
- 18a Gong J, Fuchs PL. J. Am. Chem. Soc. 1996; 118: 4486
- 18b Xiang J, Fuchs PL. J. Am. Chem. Soc. 1996; 118: 11986
- 18c Xiang J, Jiang W, Gong J, Fuchs PL. J. Am. Chem. Soc. 1997; 119: 4123
- 18d Li Z, Jiang YY, Fu Y. Chem. Eur. J. 2012; 18: 4345
- 19 Typical Procedure: To a mixture of cinnamic acid (0.148 g, 1 mmol), Ni(OAc)2·4H2O (25 mg, 0.1 mmol), and N,N-dimethylacetamide (2 mL), tert-butyl hydroperoxide (0.39 g, 3 mmol, 70% in water) was added at r.t. dropwise. The resulting mixture was heated to 100 °C for 16 h, then the mixture was added to dichloromethane (40 mL) and washed with water and saturated brine. The organic solution was dried with anhydrous magnesium sulfate and the desired product was separated on a silica gel column (petroleum ether–EtOAc).