Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2015; 26(18): 2505-2511
DOI: 10.1055/s-0034-1381051
DOI: 10.1055/s-0034-1381051
account
Syntheses of Nitrogen-Containing Heterocycles via Palladium-Catalyzed Intramolecular Dehydrogenative C–H Amination
Further Information
Publication History
Received: 27 May 2015
Accepted after revision: 16 June 2015
Publication Date:
04 September 2015 (online)
Abstract
This article traces the development of catalytic, intramolecular dehydrogenative C–H amination (IDCA) reactions. Over the last 10 years, effective syntheses of carbazoles, indolines and oxindoles via palladium-catalyzed sp2 intramolecular dehydrogenative C–H amination reactions have been realized. While the corresponding amination reactions of sp3 C–H bonds are more challenging, syntheses of pyrrolidines, azetidines, β-lactams and even aziridines via this manifold have been reported.
1 Introduction
2 Intramolecular Aminations of C(sp2)–H Bonds
3 Intramolecular Aminations of C(sp3)–H Bonds
4 Conclusion
-
References
- 1 Joule JA, Mills K. Heterocyclic Chemistry . 4th ed. Blackwell; Oxford: 2000
- 2a Thansandote P, Lautens M. Chem. Eur. J. 2009; 15: 5874
- 2b Mei TS, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778
- 3 Jeffrey JL, Sarpong R. Chem. Sci. 2013; 4: 4092
- 4 Zalatan DN, Du Bois J. Top. Curr. Chem. 2010; 292: 347
- 5 Lu H.-J, Zhang XP. Chem. Soc. Rev. 2011; 40: 1899
- 6 McIntosh JA, Coelho PS, Farwell CC, Wang ZJ, Lewis JC, Brown TR, Arnold FH. Angew. Chem. Int. Ed. 2013; 52: 9309
- 7 Louillat M.-L, Patureau FW. Chem. Soc. Rev. 2014; 43: 901
- 8 Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 9 Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 10 Tsang PW. C, Zheng N, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 14560
- 11 Tsang PW. C, Munday RH, Brasche G, Zheng N, Buchwald SL. J. Org. Chem. 2008; 73: 7603
- 12 Jordan-Hore JA, Johansson CC. C, Guilas M, Beck EM, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 16184
- 13 Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14058
- 14 Miura T, Ito Y, Murakami M. Chem. Lett. 2009; 38: 328
- 15 Mei T.-S, Wang X, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 10806
- 16a Nadres ET, Daugulis O. J. Am. Chem. Soc. 2012; 134: 7
- 16b He G, Zhao Y, Zhang S, Lu C, Chen G. J. Am. Chem. Soc. 2012; 134: 3
- 17 He G, Lu C, Zhao Y, Nack WA, Chen G. Org. Lett. 2012; 14: 2944
- 18 Ye X, He Z, Ahmed T, Weise K, Akhmedov NG, Peterson JL, Shi X. Chem. Sci. 2013; 4: 3712
- 19 Mei TS, Leow D, Xiao H, Laforteza BN, Yu J.-Q. Org. Lett. 2013; 15: 3058
- 20 Wang C, Chen C, Zhang J, Han J, Wang Q, Guo K, Liu P, Guan M, Yao Y, Zhao Y. Angew. Chem. Int. Ed. 2014; 53: 9884
- 21 He Y.-P, Zhang C, Fan M, Wu Z, Ma D. Org. Lett. 2015; 17: 496
- 22 He G, Zhang S.-Y, Nack WA, Li Q, Chen G. Angew. Chem. Int. Ed. 2013; 125: 11330
- 23 Li H, Li B.-J, Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
- 24 Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118
- 25 Neumann JJ, Rakshit S, Droge T, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 6892
- 26 Li Q, Zhang S.-Y, He G, Nack WA, Chen G. Adv. Synth. Catal. 2014; 356: 1544
- 27 Sun W.-W, Cao P, Mei R.-Q, Li Y, Ma Y.-L, Wu B. Org. Lett. 2014; 16: 480
- 28 Zhang Q, Chen K, Rao W, Zhang Y, Chen F.-J, Shi B.-F. Angew. Chem. Int. Ed. 2013; 52: 13588
- 29 Wang Z, Ni J, Kuninobu Y, Kanai M. Angew. Chem. Int. Ed. 2014; 53: 3496
- 30 Wu X.-S, Zhao Y, Zhang G.-W, Ge H.-B. Angew. Chem. Int. Ed. 2014; 53: 3706
- 31 Wu X.-S, Yang K, Zhao Y, Sun H, Li G, Ge H.-B. Nat. Commun. 2015; 6: 6462
- 32 For a recent review on β-lactam synthesis via metal-catalyzed intramolecular C–H amination, see: Zhang Q, Chen K, Shi BF. Synlett. 2014; 25: 1941
- 33 McNally A, Haffemayer B, Collins BS. L, Gaunt MJ. Nature 2014; 510: 129
For reviews on heterocycle synthesis via C–H functionalization, see: