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Synthesis 2014; 46(20): 2711-2726
DOI: 10.1055/s-0034-1379217
DOI: 10.1055/s-0034-1379217
feature article
Somophilic Isocyanide Insertion: Synthesis of 6-Arylated and 6-Trifluoromethylated Phenanthridines
Authors
Weitere Informationen
Publikationsverlauf
Received: 28. Juli 2014
Accepted after revision: 05. September 2014
Publikationsdatum:
30. September 2014 (online)
Abstract
A visible-light-promoted biaryl isocyanide insertion reaction has been developed to synthesize phenanthridine derivatives. The insertion proceeds via a radical process, and diaryliodonium salts and Umemoto’s reagent were used as radical sources. A variety of 6-arylated, as well as 6-trifluoromethylated, phenanthridine derivatives were obtained smoothly in good to excellent yields under mild conditions.
Key words
insertions - arylation - heterocycles - photoredox catalysis - trifluoromethylation - isocyanidesSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000084.
- Supporting Information (PDF)
-
References
- 1 Isonitrile Chemistry . Ugi I. Academic Press; San Diego: 1971
- 2 Isocyanide Chemistry . Nenajdenko VG. Wiley-VCH; Weinheim: 2012
- 3a Ryu I, Sonoda N, Curran DP. Chem. Rev. 1996; 96: 177
- 3b Valaar T, Maes BU. W, Ruijter E, Orru RV. A. Angew. Chem. Int. Ed. 2013; 52: 7084
- 3c Qiu G, Ding Q, Wu J. Chem. Soc. Rev. 2013; 42: 5257
- 3d Lang S. Chem. Soc. Rev. 2013; 42: 4867
- 4a Ugi I, Meyr R. Angew. Chem. 1958; 70: 702
- 4b Ugi I, Meyr R, Steinbrückner G. Angew. Chem. 1959; 71: 386
- 4c Dömling A. Chem. Rev. 2006; 106: 17
- 5a Qiu G, Liu G, Pu S, Wu J. Chem. Commun. 2012; 48: 2903
- 5b Zhao J, Peng C, Liu L, Wang Y, Zhu Q. J. Org. Chem. 2010; 75: 7502
- 5c Bochatay VN, Boissarie PJ, Murphy JA, Suckling CJ, Lang S. J. Org. Chem. 2013; 78: 1471
- 5d Vlaar T, Cioc RC, Mampuys P, Maes BU. W, Orru RV. A, Ruijter E. Angew. Chem. Int. Ed. 2012; 51: 13058
- 5e Tyagi V, Khan S, Giri A, Gauniyal HM, Sridhar B, Chauhan PM. S. Org. Lett. 2012; 14: 3126
- 5f Fei X.-D, Ge Z.-Y, Tang T, Zhu Y.-M, Ji S.-J. J. Org. Chem. 2012; 77: 10321
- 5g Li Y, Zhao J, Chen H, Liu B, Jiang H. Chem. Commun. 2012; 48: 3545
- 5h Boissarie PJ, Hamilton ZE, Lang S, Murphy JA, Suckling CJ. Org. Lett. 2011; 13: 6256
- 6a Fukuyama T, Chen X, Peng G. J. Am. Chem. Soc. 1994; 116: 3127
- 6b Sumi S, Matsumoto K, Tokuyama H, Fukuyama T. Org. Lett. 2003; 5: 1891
- 6c Kobayashi S, Peng G, Fukuyama T. Tetrahedron Lett. 1999; 40: 1519
- 6d Rainier JD, Kennedy AR. J. Org. Chem. 2000; 65: 6213
- 6e Mitamura T, Iwata K, Ogawa A. Org. Lett. 2009; 11: 3422
- 6f Mitamura T, Tsuboi Y, Iwata K, Tsuchii K, Nomoto A, Sonoda M, Ogawa A. Tetrahedron Lett. 2007; 48: 5953
- 6g Bachi MD, Balanov A, Bar-Ner N. J. Org. Chem. 1994; 59: 7752
- 6h Bachi MD, Melman A. J. Org. Chem. 1995; 60: 6242
- 6i Bachi MD, Bar-Ner N, Melman A. J. Org. Chem. 1996; 61: 7116
- 6j Curran DP, Liu H. J. Am. Chem. Soc. 1992; 114: 5863
Reference Ris Wihthout Link
- 6k Josien H, Ko S.-B, Born D, Curran DP. Chem. Eur. J. 1998; 4: 67
- 7a Chan TL, Wu Y, Choy PY, Kwong FY. Chem. Eur. J. 2013; 19: 15802
- 7b Studer A, Curran DP. Angew. Chem. Int. Ed. 2011; 50: 5018
- 7c Bowman WR, Storey JM. D. Chem. Soc. Rev. 2007; 36: 1803
Reference Ris Wihthout Link
- 8a Suffness M, Cordell GA In The Alkaloids . Vol. 25. Brossi A. Academic Press; New York: 1985: 178
- 8b Nakanishi T, Suzuki M. J. Nat. Prod. 1998; 61: 1263
- 8c Nakanishi T, Suzuki M, Saimoto A, Kabasawa T. J. Nat. Prod. 1999; 62: 864
- 8d Nakanishi T, Suzuki M. Org. Lett. 1999; 1: 985
- 8e Nakanishi T, Masuda A, Suwa M, Akiyama Y, Hoshino-Abe N, Suzuki M. Bioorg. Med. Chem. Lett. 2000; 10: 2321
- 9a Abdel-Halim OB, Morikawa T, Ando S, Matsuda H, Yoshikawa M. J. Nat. Prod. 2004; 67: 7
- 9b Tsai IL, Wun MF, Teng CM, Ishikawa T, Chen IS. Phytochemistry 1998; 48: 1377
- 9c Fang SD, Wang LK, Hecht SM. J. Org. Chem. 1993; 58: 5025
- 10a Nanni D, Pareschi P, Rizzoli C, Sgarabotto P, Tundo A. Tetrahedron 1995; 51: 9045
- 10b Tobisu M, Koh K, Furukawa T, Chatani N. Angew. Chem. Int. Ed. 2012; 51: 11363
- 11a Zhang B, Mück-Lichtenfeld C, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2013; 52: 10792
- 11b Wang Q, Dong X, Xiao T, Zhou L. Org. Lett. 2013; 15: 4846
- 11c Cheng Y, Jiang H, Zhang Y, Yu S. Org. Lett. 2013; 15: 5520
- 12a Fluorine in Medicinal Chemistry and Chemical Biology. Ojima I. Wiley; Chichester: 2009
- 12b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 12c Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 12d Smart BE. J. Fluorine Chem. 2001; 109: 3
- 12e Smart BE. Chem. Rev. 1996; 96: 1555
- 13a Leifert D, Daniliuc CG, Studer A. Org. Lett. 2013; 15: 6286
- 13b Liu J, Fan C, Yin H, Qin C, Zhang G, Zhang X, Yi H, Lei A. Chem. Commun. 2014; 50: 2145
- 14a Zhang B, Daniliuc CG, Studer A. Org. Lett. 2014; 16: 250
Reference Ris Wihthout Link
- 14b Li Y, Qiu G, Ding Q, Wu J. Tetrahedron 2014; 70: 4652
- 14c Yang B, Tian Q, Yang S. Chin. J. Org. Chem. 2014; 34: 717
- 14d Gao YZ, Wu J, Xu J, Wang XR, Tang G, Zhao YF. Asian J. Org. Chem. 2014; 3: 691
- 15a Xia Z, Huang J, He Y, Zhao J, Lei J, Zhu Q. Org. Lett. 2014; 16: 2546
- 15b Gu L, Jin C, Liu J, Ding H, Fan B. Chem. Commun. 2014; 50: 4643
- 15c Xiao T, Li L, Lin G, Wang Q, Zhang P, Mao ZW, Zhou L. Green Chem. 2014; 16: 2418
- 16a Wang L, Sha W, Dai Q, Feng X, Wu W, Peng H, Chen B, Cheng J. Org. Lett. 2014; 16: 2088
- 16b Sha W, Yu J.-T, Jiang Y, Yang H, Cheng J. Chem. Commun. 2014; 50: 9179
- 16c Li Z, Fan F, Yang J, Liu ZQ. Org. Lett. 2014; 16: 3396
- 16d Cao J.-J, Zhu T.-H, Wang S.-Y, Gu Z.-Y, Wang X, Ji S.-J. Chem. Commun. 2014; 50: 6439
- 16e Zhu Z.-Q, Wang T.-T, Bai P, Huang Z.-Z. Org. Biomol. Chem. 2014; 12: 5839
- 17a Pan C, Han J, Zhang H, Zhu C. J. Org. Chem. 2014; 79: 5374
- 17b Pan C, Han J, Zhu C. Sci. China: Chem. 2014; 57: 1
- 17c Li X, Fang M, Hu P, Hong G, Tang Y, Xu X. Adv. Synth. Catal. 2014; 356: 2103
- 18a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
- 18b Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
Reference Ris Wihthout Link
- 18c Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
Reference Ris Wihthout Link
- 18d Shi L, Xia W. Chem. Soc. Rev. 2012; 41: 7687
- 18e Xuan J, Xiao WJ. Angew. Chem. Int. Ed. 2012; 51: 6828
- 18f Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
- 18g Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 18h Hari DP, König B. Angew. Chem. Int. Ed. 2013; 52: 4734
- 19a Jiang H, Cheng Y, Wang R, Zheng M, Zhang Y, Yu S. Angew. Chem. Int. Ed. 2013; 52: 13289
- 19b Sun X, Yu S. Org. Lett. 2014; 16: 2938
- 20a Jiang H, Cheng Y, Wang R, Zhang Y, Yu S. Chem. Commun. 2014; 50: 6164
- 20b Fumagalli G, Boyd S, Greaney MF. Org. Lett. 2013; 15: 4398
- 20c Neufeldt SR, Sanford MS. Adv. Synth. Catal. 2012; 354: 3517
- 20d Lalevée J, Blanchard N, Tehfe M.-A, Morlet-Savary F, Fouassier JP. Macromolecules 2010; 43: 10191
- 21a Koike T, Akita M. Top. Catal. 2014; 57: 967
- 21b Yasu Y, Arai Y, Tomita R, Koike T, Akita M. Org. Lett. 2014; 16: 780
- 21c Mizuta S, Verhoog S, Engle KM, Khotavivattana T, O’Duill M, Wheelhouse K, Rassias G, Médebielle M, Gouverneur V. J. Am. Chem. Soc. 2013; 135: 2505
- 21d Yasu Y, Koike T, Akita M. Org. Lett. 2013; 15: 2136
- 21e Yasu Y, Koike T, Akita M. Angew. Chem. Int. Ed. 2012; 51: 9567
- 22 Kamer PC. J, Nolte RJ. M, Drenth W. J. Am. Chem. Soc. 1988; 110: 6818
For selected reviews on isocyanide insertions, see:
For selected examples of palladium-catalyzed isocyanide insertions, see:
For selected examples of somophilic isocyanide insertions, see:
For reviews on homolytic aromatic substitution, see:
For selected reviews on visible-light photoredox catalysis, see: