发展了Yb(OTf)3催化的碳氢键活化2-甲基氮杂芳烃或4-甲基氮杂芳烃对靛红的加成反应,对不同靛红和氮杂芳烃都取得了较好的产率.该方法能够一步快速合成具有重要生理活性的氮杂芳烃取代的3-羟基-2-氧化吲哚类化合物,同时该反应成功扩展了路易斯酸在sp3碳氢键活化中的应用.
参考文献
| [1] | Tobisu M;Chatani N .[J].Angew Chem Int Ed Int Ed,2006,45:1683. |
| [2] | Campos KR .Direct sp(3) C-H bond activation adjacent to nitrogen in heterocycles[J].Chemical Society Reviews,2007(7):1069-1084. |
| [3] | Jazzar, R;Hitce, J;Renaudat, A;Sofack-Kreutzer, J;Baudoin, O .Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp(3))-H Activation[J].Chemistry: A European journal,2010(9):2654-2672. |
| [4] | Ramirez TA;Zhao B;Shi Y .[J].Chemical Society Reviews,2012,41:931. |
| [5] | Campeau LC;Bertrand-Laperle M;Leclerc JP;Villemure E;Gorelsky S;Fagnou K .C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions[J].Journal of the American Chemical Society,2008(11):3276-3277. |
| [6] | Campeau, LC;Schipper, DJ;Fagnou, K .Site-selective Sp(2) and benzylic Sp(3) palladium-catalyzed direct arylation[J].Journal of the American Chemical Society,2008(11):3266-3267. |
| [7] | Kanyiva K S;Nakao Y;Hiyama T .[J].Angewandte Chemie International Edition,2007,46:8872. |
| [8] | Cho SH;Hwang SJ;Chang S .Palladium-catalyzed C-H functionalization of pyridine N-oxides: Highly selective alkenylation and direct arylation with unactivated arenes[J].Journal of the American Chemical Society,2008(29):9254-9256. |
| [9] | Larivée A;Mousseau J J;Charette A B .[J].Journal of the American Chemical Society,2008,130:52. |
| [10] | Mousseau J J;Bull J A;Charette A B .[J].Angewandte Chemie International Edition,2010,49:1115. |
| [11] | Tobisu, M;Hyodo, I;Chatani, N .Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C-H Bond Arylation of Electron-Deficient Heteroaromatic Compounds[J].Journal of the American Chemical Society,2009(34):12070-12071. |
| [12] | Nakao Y;Kanyiva KS;Hiyama T .A strategy for C-H activation of pyridines: Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis[J].Journal of the American Chemical Society,2008(8):2448-2449. |
| [13] | Deng G;Li C-J .[J].Organic Letters,2009,11:1171. |
| [14] | Qian B;Guo S;Shao J;Zhu Q Yang L Xia C Huang H .[J].Journal of the American Chemical Society,2010,132:3650. |
| [15] | Qian B;Guo S;Xia C;Huang H .[J].Advanced Synthesis and Catalysis,2010,352:3195. |
| [16] | Rueping, M.;Tolstoluzhsky, N. .Copper catalyzed C-H functionalization for direct Mannich reactions[J].Organic letters,2011(5):1095-1097. |
| [17] | Shaikh R R;Mazzanti A;Petrini M;Bartoli G,Melchiorre P .[J].Angewandte Chemie International Edition,2008,47:8707. |
| [18] | Komai, H.;Yoshino, T.;Matsunaga, S.;Kanai, M. .Lewis acid catalyzed benzylic C-H bond functionalization of azaarenes: Addition to enones[J].Organic letters,2011(7):1706-1709. |
| [19] | Qian, B.;Xie, P.;Xie, Y.;Huang, H. .Iron-catalyzed direct alkenylation of 2-substituted azaarenes with N -sulfonyl aldimines via C-H bond activation[J].Organic letters,2011(10):2580-2583. |
| [20] | Yan, Y.;Xu, K.;Fang, Y.;Wang, Z. .A catalyst-free benzylic C-H bond olefination of azaarenes for direct mannich-like reactions[J].The Journal of Organic Chemistry,2011(16):6849-6855. |
| [21] | Sanchez-Sancho F;Herradon B .[J].Heterocycles,2003,60:1843. |
| [22] | Borne R F;Aboul-Enein H Y.[J].Journal of Heterocyclic Chemistry,1972:933. |
| [23] | DeLorbe, JE;Lotz, MD;Martin, SF .Concise Total Synthesis of (+/-)-Lycopladine A[J].Organic letters,2010(7):1576-1579. |
| [24] | Taber, D.F.;Guo, P.;Pirnot, M.T. .Conjugate addition of lithiated methyl pyridines to enones[J].The Journal of Organic Chemistry,2010(16):5737-5739. |
| [25] | Peddibhotla S .[J].Curr Bioact Compd,2009,5:20. |
| [26] | Galliford C V;Scheidt K A .[J].Angew Chem Int Ed Int Ed,2007,46:8748. |
| [27] | Marti C;Carreira E M.[J].European Journal of Organic Chemistry,2003:2209. |
| [28] | Zhou F;Liu Y L;Zhou J .[J].Advanced Synthesis and Catalysis,2010,352:1381. |
| [29] | Niu, R.;Xiao, J.;Liang, T.;Li, X. .Facile synthesis of azaarene-substituted 3-hydroxy-2-oxindoles via Br?nsted acid catalyzed sp ~3 C - H functionalization[J].Organic letters,2012(3):676-679. |
| [30] | Pieper U;Stalke D .[J].Organometallics,1993,12:1201. |
| [31] | Leung W-P;Lee H K;Weng L-H;Luo B S Zhou Z-Y Mak T C W .[J].Organometallics,1996,15:1785. |
| [32] | Andrews P C;Armstrong D R;Raston C L;Roberts B A,Skelton B W,White A H.[J].Journal of the Chemical Society,Dalton Transactions,2001:996. |
| [33] | Thomas D.;Spannenberg A.;Kempe R.;Rosenthal U.;Baumann W. .Zirconocene and rac-[1,2-ethylene-1,1 '-bis(eta(5)-tetrahydroindenyl)]zirconium complexes of 2-vinylpyridine: Syntheses, X-ray crystal structures, and reactions with H2C=CH2, H2O, HBF4, and CO2[J].Organometallics,1998(10):2096-2102. |
| [34] | Niwa T;Yorimitsu H;Oshima K .[J].Angewandte Chemie International Edition,2007,46:2643. |
| [35] | Shang, R.;Yang, Z.-W.;Wang, Y.;Zhang, S.-L.;Liu, L. .Palladium-catalyzed decarboxylative couplings of 2-(2-Azaaryl)acetates with aryl halides and triflates[J].Journal of the American Chemical Society,2010(41):14391-14393. |
| [36] | Song G Y;Su Y;Gong X;Han K L Li X W .[J].Organic Letters,2011,13:1968. |
| [37] | Wei X H;Zhao M;Du Z Y;Li X .[J].Organic Letters,2011,13:4636. |
| [38] | Gong, X.;Song, G.;Zhang, H.;Li, X. .Palladium-catalyzed oxidative cross-coupling between pyridine N-oxides and indoles[J].Organic letters,2011(7):1766-1769. |
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