Recent Development in N-Auxilixary-Assisted Intramolecular Amination for Amine Substrates

Abstract

Direct coupling of N–H with C–H has aroused great attention in the last decades; during which the directing-group-assisted intramolecular C–N bond formation via transition metal has been achieved significant progress. Herein, we highlight the recent development in the directing-group-assisted intramolecular amination for amine substrates to build the important N-containing heterocyclic compounds.

1 Introduction

2 Triflamide-Promoted Intramolecular Amination

3 Picolinamide-Assisted Intramolecular Amination

4 Palladium-Catalyzed Intramolecular Amination under Assistance of Oxalyl Amide

5 Conclusion

Key words

amination - cyclization - transition metals - C–H activation - directing groups

• References

• 1a Jensen T, Fristrup P. Chem. Eur. J. 2009; 15: 9632
• 1b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 1c Bras JL, Muzart J. Chem. Rev. 2011; 111: 1170
• 1d Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
• 1e Broggini G, Beccalli EM, Fasana A, Gazzola S. Beilstein J. Org. Chem. 2012; 8: 1730
• 1f Yuan J, Liu C, Lei A. Chem. Commun. 2015; 51: 1394
• 2a Dick AR, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004; 126: 2300
• 2b Hull KL, Lanni EL, Sanford MS. J. Am. Chem. Soc. 2006; 128: 14047
• 2c Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
• 3a Desai LV, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004; 126: 9542
• 3b Thu H.-Y, Yu W.-Y, Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
• 3c Kang T, Kim Y, Lee D, Wang Z, Chang S. J. Am. Chem. Soc. 2014; 136: 4141
• 3d Ren Z, Mo F, Dong G. J. Am. Chem. Soc. 2012; 134: 16991
• 4a Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
• 4b Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z. J. Am. Chem. Soc. 2006; 128: 7416
• 4c Wasa M, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 9886
• 4d Wang D.-H, Hao X.-S, Wu D.-F, Yu J.-Q. Org. Lett. 2006; 8: 3387
• 5a Giri R, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14082
• 5b Wang D.-H, Engle KM, Shi B.-F, Yu J.-Q. Science 2010; 327: 315
• 6a Lu Y, Wang D.-H, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 5916
• 6b Wang X, Lu Y, Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 12203
• 6c Xiao B, Gong T.-J, Liu Z.-J, Liu J.-H, Luo D.-F, Xu J, Liu L. J. Am. Chem. Soc. 2011; 133: 9250
• 7a Giri R, Liang J, Lei J.-G, Li J.-J, Wang D.-H, Chen X, Naggar IC, Guo C, Foxman BM, Yu J.-Q. Angew. Chem. Int. Ed. 2005; 44: 7420
• 7b Li G, Leow D, Wan L, Yu J.-Q. Angew. Chem. Int. Ed. 2013; 52: 1245
• 7c Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature (London, U.K.) 1993; 366: 529
• 7d Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826

For recent reviews, see:
• 8a Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826
• 8b Godula K, Sames D. Science 2006; 312: 67
• 8c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 8d MaNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
• 8e McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
• 8f Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2011; 45: 788
• 8g Li B.-J, Shi Z.-J. Chem. Soc. Rev. 2012; 41: 5588
• 8h Mousseau JJ, Charette AB. Acc. Chem. Res. 2012; 46: 412
• 8i Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 8j Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
• 8k Louillat M.-L, Patureau FW. Chem. Soc. Rev. 2014; 43: 901
• 9 Mei T.-S, Wang X, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 10806
• 10 He G, Zhao Y, Zhang S, Lu C, Chen G. J. Am. Chem. Soc. 2012; 134: 3
• 11 Nadres ET, Daugulis O. J. Am. Chem. Soc. 2012; 134: 7
• 12 Ye X, He Z, Ahmed T, Weise K, Akhmedov NG, Petersen JL, Shi X. Chem. Sci. 2013; 4: 3712
• 13 Li J.-J, Mei T.-S, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 6452
• 14 Mei T.-S, Leow D, Xiao H, Laforteza BN, Yu J.-Q. Org. Lett. 2013; 15: 3058
• 15 Yang M, Su B, Wang Y, Chen K, Jiang X, Zhang Y.-F, Zhang X.-S, Chen G, Cheng Y, Cao Z, Guo Q.-Y, Wang L, Shi Z.-J. Nat. Commun. 2014; 5: 4707
• 16 He G, Lu C, Zhao Y, Nack WA, Chen G. Org. Lett. 2012; 14: 2944
• 17 Wang C, Chen CP, Zhang JY, Han J, Wang Q, Guo K, Liu P, Guan MY, Yao YM, Zhao YS. Angew. Chem. Int. Ed. 2014; 53: 9884
• 18a Wang Q, Han J, Wang C, Zhang JY, Huang ZB, Shi DQ, Zhao YS. Chem. Sci. 2014; 5: 4962
• 18b Han J, Liu P, Wang C, Wang Q, Zhang JY, Zhao YW, Shi DQ, Huang ZB, Zhao YS. Org. Lett. 2014; 16: 5682