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-00000084.xml
Synthesis 2014; 46(08): 1067-1072
DOI: 10.1055/s-0033-1340832
DOI: 10.1055/s-0033-1340832
paper
Palladium-Catalyzed Intramolecular Direct Arylation for Phosphorus Heterocycle Synthesis
Further Information
Publication History
Received: 06 December 2013
Accepted after revision: 27 January 2014
Publication Date:
18 February 2014 (online)
Abstract
A palladium-catalyzed intramolecular direct arylation of bromo-substituted phosphine oxides is reported for the synthesis of phosphorus-containing heterocycles with good to excellent yields (78–98%)
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826
- 1b Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
- 1c Li B, Yang S, Shi Z. Synlett 2008; 949
-
1d Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
- 1e Ackermann L, Vicente R, Kapdi A. Angew. Chem. Int. Ed. 2009; 48: 9792
- 1f Xu L.-M, Li B.-J, Yang Z, Shi Z.-J. Chem. Soc. Rev. 2010; 39: 712
- 1g Albrecht M. Chem. Rev. 2010; 110: 576
-
1h Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
-
1i Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 1j Ackermann L. Chem. Rev. 2011; 111: 1315
- 1k Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
- 1l Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
- 2a Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 2b Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
- 2c Stokes BJ, Briver TG. Eur. J. Org. Chem. 2011; 4071
- 2d Mei T.-S, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778
- 2e Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 2f Wencel-Delord J, Glorius F. Nature Chem. 2012; 5: 369
- 2g Yoshikai N, Wei Y. Asian J. Org. Chem. 2013; 2: 466
- 3a Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications. Vols. 1–3. Börner A. Wiley-VCH; Weinheim: 2008
- 3b Phosphorus Heterocycles II. In Topics in Heterocyclic Chemistry. Vol 21. Bansal RK. Springer; Berlin: 2010
- 3c Phosphorus Compounds. In Advanced Tools in Catalysis and Material Sciences. Peruzzini M, Gonsalvi L. Springer; Berlin: 2011
- 4a Kuninobu Y, Yoshida T, Takai K. J. Org. Chem. 2011; 76: 7370
- 4b Hou C, Ren Y, Lang R, Hu X, Xia C, Li F. Chem. Commun. 2012; 48: 5181
- 4c Feng C.-G, Ye M, Xiao K.-J, Li S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 9322
- 4d Meng X, Kim S. Org. Lett. 2013; 15: 1910
- 4e Chan LY, Kim S, Ryu T, Lee PH. Chem. Commun. 2013; 49: 4682
- 4f Chan L, Cheong L, Kim S. Org. Lett. 2013; 15: 2186
- 4g Chary BC, Kim S, Park Y, Kim J, Lee PH. Org. Lett. 2013; 15: 2692
-
4h Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 3258
- 4i Seo J, Park Y, Jeon I, Ryu T, Park S, Lee PH. Org. Lett. 2013; 15: 3358
- 4j Chan LY, Meng XJ, Kim S. J. Org. Chem. 2013; 78: 8826
- 4k Zhao D, Nimphius C, Lindale M, Glorius F. Org. Lett. 2013; 15: 4504
- 4l Jeon WH, Lee TS, Kim EJ, Moon B, Kang J. Tetrahedron 2013; 69: 5152
- 4m Itoh M, Hashimoto Y, Hirano K, Satoh T, Miura M. J. Org. Chem. 2013; 78: 8098
- 4n Li C, Yano T, Ishida N, Murakami M. Angew. Chem. Int. Ed. 2013; 52: 9801
- 4o Baba K, Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11892
- 4p Wang H.-Li, Hu R.-B, Zhang H, Zhou A.-X, Yang S.-D. Org. Lett. 2013; 15: 5302
-
4q Zhang H.-Y, Yi H.-M, Wang G.-W, Yang B, Yang S.-D. Org. Lett. 2013; 15: 6186
- 5a Tayama O, Nakano A, Iwahama T, Sakaguchi S, Ishii Y. J. Org. Chem. 2004; 69: 5494
-
5b Kagayama T, Nakano A, Sakaguchi S, Ishii Y. Org. Lett. 2006; 8: 407
- 5c Mu X.-J, Zou J.-P, Qian Q.-F, Zhang W. Org. Lett. 2006; 8: 5291
- 5d Pan X.-Q, Zou J.-P, Zhang G.-L, Zhang W. Chem. Commun. 2010; 46: 1721
- 5e Zhou J, Zhang Z.-G, Zou J.-P, Zhang W. Eur. J. Org. Chem. 2011; 3412
- 5f Pan X.-Q, Wang L, Zou J.-P, Zhang W. Chem. Commun. 2011; 47: 7875
- 5g Wang C.-B, Bian Y.-J, Mao X.-R, Huang Z.-Z. J. Org. Chem. 2012; 77: 7706
- 5h Wang H, Li X, Wu F, Wan B. Synthesis 2012; 44: 941
- 5i Li Y.-M, Sun M, Wang H.-L, Ting Q.-P, Yang S.-D. Angew. Chem. Int. Ed. 2013; 52: 3972
- 5j Chen Y.-R, Duan W.-L. J. Am. Chem. Soc. 2013; 135: 16754
- 5k Unoh Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 12975
- 6a Campeau L.-C, Fagnou K. Chem. Commun. 2006; 1253
- 6b Campeau L.-C, Fagnou K. Chem. Soc. Rev. 2007; 36: 1058
- 6c Lafrance M, Lapointe D, Fagnou K. Tetrahedron 2008; 64: 6015
- 7a Grabulosa A, Granell J, Muller G. Coord. Chem. Rev. 2007; 251: 25
- 7b Kolodiazhnyi OI. Tetrahedron: Asymmetry 2012; 23: 1
- 7c Xu Q, Zhao C.-Q, Han L.-B. J. Am. Chem. Soc. 2008; 130: 12648
- 7d Berger O, Montchamp J.-L. Angew. Chem. Int. Ed. 2013; 52: 11377
- 8 Glorius F, Altenhoff G, Goddard R, Lehmann C. Chem. Commun. 2002; 2704
For selected reviews on C–H bond functionalization, see:
For selected reviews on the synthesis of heterocycles through C–H bond activation strategy, see:
For the synthesis of phosphorus heterocycles through radical pathways, see:
For the use of palladium-catalyzed direct arylation for the synthesis of oxygen or nitrogen heterocycles, see:
For selected examples on the functionalization of arylphosphinates, see: