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Synthesis 2014; 46(17): 2297-2304
DOI: 10.1055/s-0033-1338630
DOI: 10.1055/s-0033-1338630
special topic
Silver-Mediated Alkyne Annulations by C–H/P–H Functionalizations: Step-Economical Access to Benzophospholes
Further Information
Publication History
Received: 01 March 2014
Accepted: 03 April 2014
Publication Date:
30 April 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201417/lookinside/thumbnails/10.1055-s-0033-1338630-1.jpg)
Abstract
Silver-mediated alkyne annulations by secondary phosphine oxides (SPOs) or arylphosphinates via C–H/P–H functionalization provided versatile access to substituted benzo[b]phospholes in a step-economical fashion.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Stolar M., Baumgartner T.; Chem. Asian J.; 2014, 9: in press; DOI: 10.1002/asia.201301670.
- 1b He X, Woo AY. Y, Borau-Garcia J, Baumgartner T. Chem. Eur. J. 2013; 19: 7620
- 1c Ren Y, Baumgartner T. J. Am. Chem. Soc. 2011; 133: 1328
- 1d Matano Y, Saito A, Fukushima T, Tokudome Y, Suzuki F, Sakamaki D, Kaji H, Ito A, Tanaka K, Imahori H. Angew. Chem. Int. Ed. 2011; 50: 8016
- 1e Ren Y, Kan WH, Henderson MA, Bomben PG, Berlinguette CP, Thangadurai V, Baumgartner T. J. Am. Chem. Soc. 2011; 133: 17014
- 1f Sanji T, Shiraishi K, Tanaka M. Org. Lett. 2007; 9: 3611
- 1g Lampin J.-P, Mathey F. J. Organomet. Chem. 1974; 71: 239
- 2a Hayashi Y, Matano Y, Suda K, Kimura Y, Nakao Y, Imahori K. Chem. Eur. J. 2012; 18: 15972
- 2b Fukazawa A, Ichihashi Y, Kosaka Y, Yamaguchi S. Chem. Asian J. 2009; 4: 1729
- 2c Tsuji H, Sato K, Ilies L, Itoh Y, Sato Y, Nakamura E. Org. Lett. 2008; 10: 2263
- 2d Sanji T, Shiraishi K, Kashiwabara T, Tanaka M. Org. Lett. 2008; 10: 2689
- 2e Märkl G, Jin GY, Berr K.-P. Tetrahedron Lett. 1993; 34: 3103
- 2f Balthazor TM. J. Org. Chem. 1980; 45: 2519
- 4a Girard SA, Knauber T, Li CJ. Angew. Chem. Int. Ed. 2014; 53: 74
- 4b Thirunavukkarasu VS, Kozhushkov SI, Ackermann L. Chem. Commun. 2014; 50: 29
- 4c Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
- 4d Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 4e Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
- 4f Ackermann L. Chem. Rev. 2011; 111: 1315
- 4g Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
- 5a Ackermann L. Acc. Chem. Res. 2014; 47: 281
- 5b Arockiam P, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 5c Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
- 5d Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212 ; and references cited therein
- 5e Song W, Ackermann L. Chem. Commun. 2013; 49: 6638
- 5f Baba K, Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2013; 53: 11892
- 5g Wang H, Grohmann C, Nimphius C, Glorius F. J. Am. Chem. Soc. 2012; 134: 19592
- 5h Ma W, Graczyk K, Ackermann L. Org. Lett. 2012; 14: 6318
- 5i Morimoto K, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 9548
- 5j Huestis MP, Chan LN, Stuart DR, Fagnou K. Angew. Chem. Int. Ed. 2011; 50: 11338
- 5k Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14952
- 5l Chen J, Song G, Pan C.-L, Li X. Org. Lett. 2010; 12: 5426
- 5m Stuart DR, Bertrand-Laperle M, Burgess KM. N, Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
- 5n Ueura K, Satoh T, Miura M. Org. Lett. 2007; 9: 1407
- 6a Park Y, Seo J, Park S, Yoo EJ, Lee PH. Chem. Eur. J. 2013; 19: 16461
- 6b Zhao DC, Nimphius C, Lindale M, Glorius F. Org. Lett. 2013; 15: 4504
- 6c Ryu T, Kim J, Park Y, Kim S, Lee PH. Org. Lett. 2013; 15: 3986
- 6d Seo J, Park Y, Jeon I, Ryu T, Park S, Lee PH. Org. Lett. 2013; 15: 3358
- 6e Park S, Seo B, Shin S, Son J.-Y, Lee PH. Chem. Commun. 2013; 49: 8671
-
6f Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 3258
- 6g Itoh M, Hashimoto Y, Hirano K, Satoh T, Miura M. J. Org. Chem. 2013; 78: 8098
- 6h Kuninobu Y, Yoshida T, Takai K. J. Org. Chem. 2011; 76: 7370
- 7 Ackermann L. Pure Appl. Chem. 2010; 82: 1403
- 8a Ackermann L, Barfüsser S, Kornhaass C, Kapdi AR. Org. Lett. 2011; 13: 3082
- 8b Ackermann L, Kapdi AR, Fenner S, Kornhaaß C, Schulzke C. Chem. Eur. J. 2011; 17: 2965
- 8c Ackermann L, Born R, Spatz JH, Meyer D. Angew. Chem. Int. Ed. 2005; 44: 7216
- 8d Ackermann L. Org. Lett. 2005; 7: 3123
- 8e Ackermann L, Born R. Angew. Chem. Int. Ed. 2005; 44: 2444
- 8f Ackermann L. Isr. J. Chem. 2010; 50: 652
- 8g Ackermann L. Synthesis 2006; 1557
-
9a He C, Guo S, Ke J, Hao J, Xu H, Chen H, Lei A. J. Am. Chem. Soc. 2012; 134: 5766
- 9b He C, Hao J, Xu H, Mo Y, Liu H, Han J, Lei A. Chem. Commun. 2012; 48: 11073
- 10a Chen Y, Duan W. J. Am. Chem. Soc. 2013; 135: 16754
- 10b Unoh Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 12975
- 11 Deponti M, Kozhushkov SI, Yufit DS, Ackermann L. Org. Biomol. Chem. 2013; 11: 142 ; and references cited therein
For a recent review, see:
For selected examples, see:
For selected recent reviews on C–H functionalizations, see:
For selected recent reviews on metal-catalyzed oxidative alkyne annulations, see:
For selected examples, see:
Recent examples: rhodium catalysis:
Ruthenium catalysis:
Palladium catalysis:
Representative examples:
Reviews:
Two related studies were reported during the preparation of this manuscript, see: