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Synlett 2011(20): 2991-2994
DOI: 10.1055/s-0031-1289883
DOI: 10.1055/s-0031-1289883
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Iron-Mediated Cyanation of Methoxybenzene, Indole, and 2-Arylpyridine C-H Bonds
Further Information
Received
4 September 2011
Publication Date:
11 November 2011 (online)
Publication History
Publication Date:
11 November 2011 (online)
Abstract
An iron-mediated direct cyanation of indole and 2-arylpyridine C-H bonds is described. Notably, trimethoxybenzene reacted smoothly under the procedure, forming a C-CN bond via C-H bond cleavage without chelation assistance.
Key words
iron - indole - 2-arylpyridine - C-H activation - cyanation
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Nagamura S.Kobayashi E.Gomi K.Saito H. Bioorg. Med. Chem. 1996, 4: 1379 -
1b
Kleemann A.Engel J.Kutscher B.Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications 4th ed.: Thieme; Stuttgart: 2001. -
1c
Murdoch D.Keam S. Drugs 2005, 65: 2379 -
1d
Njar VCO.Brodie AMH. Drugs 1999, 58: 233 -
2a
The Chemistry of the Cyano Group
Rappoport Z. Wiley; London: 1970. -
2b
Larock RC. Comprehensive Organic Transformations Wiley-VCH; New York: 1989. p.819-995 -
2c
Ju Y.Liu F.Li C. Org. Lett. 2009, 11: 3582 -
3a
Sandmeyer T. Ber. Dtsch. Chem. Ges. 1884, 17: 2650 -
3b
Hodgson HH. Chem. Rev. 1947, 40: 251 -
3c
Galli C. Chem. Rev. 1988, 88: 765 -
3d
Bohlmann R. In Comprehensive Organic Synthesis Vol. 6:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.203 -
4a
Friedrich K.Wallenfels K. In The Chemistry of the Cyano Group Wiley; New York: 1970. p.77-86 -
4b
Friedrich K. In The Chemistry of Functional Groups Wiley; New York: 1970. p.1345-1390; Suppl. C -
4c
Wu J.Beck B.Ren R. Tetrahedron Lett. 2002, 43: 387 -
4d
Wang D.Kuang L.Li Z.Ding K. Synlett 2008, 69 - Review:
-
5a
Anbarasan P.Schareina T.Beller M. Chem. Soc. Rev. 2011, 40: 5409 - For selected reports on palladium-catalyzed cyanation of aryl halides, see:
-
5b
Hatsuda M.Seki M. Tetrahedron 2005, 61: 9908 -
5c
Jensen RS.Gajare AS.Toyota K.Yoshifuji K.Ozawa F. Tetrahedron Lett. 2005, 46: 8645 -
5d
Schareina T.Zapf A.Beller M. Chem. Commun. 2004, 1388 -
5e
Weissman SA.Zewge D.Chen C. J. Org. Chem. 2005, 70: 1508 -
5f
Grossman O.Gelman D. Org. Lett. 2006, 8: 1189 -
5g
Mariampillai B.Alberico D.Bidau V.Lautens M.
J. Am. Chem. Soc. 2006, 128: 14436 -
5h
Mariampillai B.Alliot J.Li M.Lautens M. J. Am. Chem. Soc. 2007, 129: 15372 -
5i
Littke A.Soumeillant M.Kaltenbach RF.Cherney RJ.Tarby CM.Kiau S. Org. Lett. 2007, 9: 1711 -
5j
Yeung PY.So CM.Lau CP.Kwong FY. Org. Lett. 2011, 13: 648 -
5k
Yu H.Richey RN.Miller WD.Xu J.May SA. J. Org. Chem. 2011, 76: 665 -
5l
Yeung PY.Tsang CP.Kwong FY. Tetrahedron Lett. 2011, in press; DOI: 10.1016/j.tetlet.2011.09.088 - For selected reports on copper-catalyzed or copper-mediated cyanation of aryl halides, see:
-
6a
Zanon J.Klapars A.Buchwald S. J. Am. Chem. Soc. 2003, 125: 2890 -
6b
Cristau H.-J.Ouali A.Spindler J.-F.Taillefer M. Chem. Eur. J. 2005, 11: 2483 -
6c
Schareina T.Zapf A.Beller M. Tetrahedron Lett. 2005, 46: 2585 -
6d
Schareina T.Zapf A.Mägerlein W.Müller N.Beller M. Chem. Eur. J. 2007, 13: 6249 -
6e
Schareina T.Zapf A.Mägerlein W.Müller N.Beller M. Synlett 2007, 555 -
6f
Ren Y.Wang W.Zhao S.Tian X.Wang J.Yin W.Cheng L. Tetrahedron Lett. 2009, 50: 4595 -
6g
Zhang G.Ren X.Chen J.Hu M.Cheng J. Org. Lett. 2011, 13: 5004 - For the cyanation of organoboron, see ref. 18 and:
-
7a
Zhang ZH.Liebeskind LS. Org. Lett. 2006, 8: 4331 -
7b
Zhang G.Zhang L.Hu M.Cheng J. Adv. Synth. Catal. 2011, 353: 291 -
7c
Anbarasan P.Neumann H.Beller M. Angew. Chem. Int. Ed. 2011, 50: 519 - For selected reviews on C-H functionalization, please see:
-
8a
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 -
8b
Chen X.Engle KM.Wang D.-H.Yu J.-Q. Angew. Chem. Int. Ed. 2009, 48: 5094 -
8c
Yeung CS.Dong VM. Chem. Rev. 2011, 111: 1215 - For selected reports on C-H functionalization, please see:
-
8d
Lu Y.Leow D.Wang X.Engle KM.Yu J.-Q. Chem. Sci. 2011, 2: 967 -
8e
Li B.-J.Shi Z.-J. Chem. Sci. 2011, 2: 488 -
8f
Tang B.-X.Song R.-J.Wu C.-Y.Liu Y.Zhou M.-B.Wei W.-T.Deng G.-B.Yin D.-L.Li J.-H. J. Am. Chem. Soc. 2010, 132: 8900 -
8h
Wang G.-W.Yuan T.-T.Li D.-D. Angew. Chem. Int. Ed. 2011, 50: 1380 -
8i
Kwak J.Kim M.Chang S. J. Am. Chem. Soc. 2011, 133: 3780 - 9
Chen X.Hao X.-S.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790 -
10a
Jia X.Yang D.Zhang S.Cheng J. Org. Lett. 2009, 11: 4716 -
10b
Jia X.Yang D.Wang W.Luo F.Cheng J. J. Org. Chem. 2009, 74: 9470 - 11
Kim J.Chang S. J. Am. Chem. Soc. 2010, 132: 10272 - 12
Do H.-Q.Daugulis O. Org. Lett. 2010, 12: 2517 - 13
Subba Reddy B.Begum VZ.Jayasudhan Reddy YJ. Tetrahedron Lett. 2010, 51: 3334 - 14
Yan G.Kuang C.Zhang Y.Wang J. Org. Lett. 2010, 12: 1052 - 15
Ding ST.Jiao N. J. Am. Chem. Soc. 2011, 133: 12374 - 16
Ren X.Chen J.Chen F.Cheng J. Chem. Commun. 2011, 47: 6725 - 18
Liskey CW.Liao X.Hartwig JF. J. Am. Chem. Soc. 2010, 132: 11389 -
19a
Bolm C.Legros J.Paih JL.Zani L. Chem. Rev. 2004, 104: 6217 -
19b
Correa A.Mancheńo OG.Bolm C. Chem. Soc. Rev. 2008, 37: 1108 -
19c
Enthaler S.Junge K.Beller M. Angew. Chem. Int. Ed. 2008, 47: 3317 -
19d
Sherry BD.Fürstner A. Acc. Chem. Res. 2008, 41: 1500 -
19e
Sarhan AAO.Bolm C. Chem. Soc. Rev. 2009, 38: 2730 -
19f
Sun C.-L.Li B.-J.Shi Z.-J. Chem. Rev. 2011, 111: 1293 -
20a
Vallée F.Mousseau JJ.Charette AB. J. Am. Chem. Soc. 2010, 132: 1514 -
20b
Li Y.-Z.Li B.-J.Lu X.-Y.Lin S.Shi Z.-J. Angew. Chem. Int. Ed. 2009, 48: 3817 -
20c
Song CX.Cai GX.Farrell TR.Jiang ZP.Li H.Gan LB.Shi Z.-J. Chem. Commun. 2009, 6002 -
20d
Li Z.Cao L.Li C.-J. Angew. Chem. Int. Ed. 2007, 46: 6505 -
20e
Li Z.Yu R.Li H. Angew. Chem. Int. Ed. 2008, 47: 7497 -
20f
Zhang Y.Li C.-J. Eur. J. Org. Chem. 2007, 4654 -
20g
Wen J.Zhang J.Chen S.-Y.Li J.Yu X.-Q. Angew. Chem. Int. Ed. 2008, 47: 8897 -
20h
Norinder J.Matsumoto A.Yoshikai N.Nakamura E. J. Am. Chem. Soc. 2008, 130: 5858 -
20i
Liu W.Cao H.Lei A. Angew. Chem. Int. Ed. 2010, 49: 2004 -
20j
Nakamura E.Yoshikai N. J. Org. Chem. 2010, 75: 6061 -
20k
Jones WD.Foster GP.Putinas JM. J. Am. Chem. Soc. 1987, 109: 5047 -
20l
Qin C.Jiao N. J. Am. Chem. Soc. 2010, 132: 15893 -
21a
Wang W.Pan C.Chen F.Cheng J. Chem. Commun. 2011, 47: 3978 -
21b
Jia X.Zhang S.Wang W.Luo F.Cheng J. Org. Lett. 2009, 11: 3120 -
21c
Ye Z.Wang W.Luo F.Zhang S.Cheng J. Org. Lett. 2009, 11: 3974 -
21d
Wang W.Luo F.Zhang S.Cheng J. J. Org. Chem. 2010, 75: 2415 -
21e
Zhang S.Qian P.Zhang M.Hu M.Cheng J. J. Org. Chem. 2010, 75: 6732 -
21f
Zhang S.Luo F.Wang W.Jia X.Hu M.Cheng J. Tetrahedron Lett. 2010, 51: 33172
References and Notes
Wang reported the Pd-catalyzed cyanation of trimethoxybenzene, providing the product in 35% yield; see ref. 14.
22For the transition-metal-catalyzed 2-aryl pyridine sp² C-H cyanation, please see ref. 9-11.