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
References and Notes
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
5a Anbarasan P.
Schareina T.
Beller M.
Chem. Soc.
Rev.
2011,
40:
5409
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.
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
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
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
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
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
17 Wang reported the Pd-catalyzed cyanation
of trimethoxybenzene, providing the product in 35% yield;
see ref. 14.
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
22 For the transition-metal-catalyzed
2-aryl pyridine sp² C-H cyanation,
please see ref. 9-11.
