描述了一种采用三价铑催化的醛的氧化胺化反应，利用Ag2CO3作为氧化剂。通过该方法可以以良好的收率合成各种类型的N-吡啶酰胺及酰亚胺。
A novel Rh(III)-catalyzed direct amidation of aldehydes featuring Ag2CO3 as the oxidant is described. This selective procedure provides a variety of N-pyridinamides and imide derivatives in good yields.
参考文献
| [1] | Fraxedas J;Molecular Organic Materials:From Molecules to Crys-talline Solids.[M].Cambridge:Cambridge Univer Press,2008 |
| [2] | Bode JW .Emerging methods in amide- and peptide-bond formation.[J].Current opinion in drug discovery & development,2006(6):765-775. |
| [3] | Cupido T;Tulla-Puche J;Spengler J;Albericio F .The synthesis of naturally occurring peptides and their analogs.[J].Current opinion in drug discovery & development,2007(6):768-783. |
| [4] | Pandey J;Sharma A;Tiwari V K;Dube D Ramachandran R Cha-turvedi V Sinha S Mishra N N Shukla P K Tripathi R P J .[J].Comb Chem,2009,11:422. |
| [5] | 盛国柱,张炜.酰胺官能团构建方法研究新进展[J].有机化学,2013(11):2271-2282. |
| [6] | 杨敏,李敏,郑宏杰,李贤均.钨酸钠催化芳香腈高选择性氧化制备芳香酰胺[J].催化学报,2005(03):175-177. |
| [7] | 胡金金,左秀锦,黄汉民.基于C-H键活化的铜催化二苄胺氧化酰胺化反应[J].催化学报,2013(09):1644-1650. |
| [8] | Montalbetti C A G N;Falque V .[J].Tetrahedron,2005,61:10827. |
| [9] | Valeur E;Bradley M .[J].CHEMICAL SOCIETY REVIEWS,2009,38:606. |
| [10] | Bray B L .[J].Nat Rev Drug Discovery,2003,2:587. |
| [11] | Albericio F .[J].Current Opinion in Chemical Biology,2004,8:211. |
| [12] | Xiao F H;Liu Y;Tang C L;Deng G J .[J].Organic Letters,2012,14:984. |
| [13] | Ghosh, S.C.;Ngiam, J.S.Y.;Seayad, A.M.;Tuan, D.T.;Chai, C.L.L.;Chen, A. .Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides[J].The Journal of Organic Chemistry,2012(18):8007-8015. |
| [14] | Kuwano, S.;Harada, S.;Oriez, R.;Yamada, K.-I. .Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis[J].Chemical communications,2012(1):145-147. |
| [15] | Zhang, B.;Feng, P.;Cui, Y.;Jiao, N. .NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters, amides[J].Chemical communications,2012(58):7280-7282. |
| [16] | Ghosh S C;Ngiam J S Y;Chai C L L;Seayad A M Dang T T Chen A Q .[J].Advanced Synthesis and Catalysis,2012,354:1407. |
| [17] | Fu Z Q;Lee J;Kang B;Hong S H .[J].Organic Letters,2012,14:6028. |
| [18] | Malineni J;Merkens C;Keul H;M?ller M .[J].CATALYSIS COMMUNICATIONS,2013,40:80. |
| [19] | Li H M;Xie J;Xue Q C;Cheng Y X Zhu C J .[J].Tetrahedron Letters,2012,53:6479. |
| [20] | Kazuya K;Hiroaki K;Takamichi O;Noritaka M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2012,51:544. |
| [21] | Gaspa S;Porcheddu A;De Luca L .[J].Organic and Biological Chemistry,2013,11:3803. |
| [22] | Kulkarni, S.S.;Hu, X.;Manetsch, R. .A simple base-mediated amidation of aldehydes with azides[J].Chemical communications,2013(12):1193-1195. |
| [23] | Carbone, G.;Burnley, J.;Moses, J.E. .A catalytic and tert-butoxide ion-mediated amidation of aldehydes with para-nitro azides[J].Chemical communications,2013(27):2759-2761. |
| [24] | Zhou, B.;Yang, Y.;Shi, J.;Feng, H.;Li, Y. .Rhodium-catalyzed synthesis of amides from aldehydes and azides by chelation-assisted C-H bond activation[J].Chemistry: A European journal,2013(32):10511-10515. |
| [25] | Ekoue-Kovi K;Wolf C .One-pot oxidative esterification and amidation of aldehydes[J].Chemistry: A European journal,2008(21):6302-6315. |
| [26] | De Sarkar, S.;Studer, A. .Oxidative amidation and azidation of aldehydes by NHC catalysis[J].Organic letters,2010(9):1992-1995. |
| [27] | Liang, J.;Lv, J.;Shang, Z.-C. .Metal-free synthesis of amides by oxidative amidation of aldehydes with amines in PEG/oxidant system[J].Tetrahedron,2011(44):8532-8535. |
| [28] | Prasad, V.;Kale, R.R.;Mishra, B.B.;Kumar, D.;Tiwari, V.K. .Diacetoxyiodobenzene mediated one-pot synthesis of diverse carboxamides from aldehydes[J].Organic letters,2012(12):2936-2939. |
| [29] | Muthaiah, S.;Ghosh, S.C.;Jee, J.-E.;Chen, C.;Zhang, J.;Hong, S.H. .Direct amide synthesis from either alcohols or aldehydes with amines: Activity of Ru(II) hydride and Ru(0) complexes[J].The Journal of Organic Chemistry,2010(9):3002-3006. |
| [30] | Li G L;Kung K K Y;Wong M K .[J].Chemistry Communications,2012,48:4112. |
| [31] | Li Y M;Jia F;Li Z P .[J].CHEMISTRY-A EUROPEAN JOURNAL,2013,19:82. |
| [32] | Tillack A;Rudloff I;Beller M.[J].EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2001:523. |
| [33] | Chan, J;Baucorn, KD;Murry, JA .Rh(II)-Catalyzed intermolecular oxidative sulfamidation of aldehydes: A mild efficient synthesis of N-sulfonylcarboxamides[J].Journal of the American Chemical Society,2007(46):14106-14107. |
| [34] | Raoufmoghaddam S;Drent E;Bouwman E .[J].Advanced Synthesis and Catalysis,2013,355:717. |
| [35] | Hiroshi F;Yoshiyuki O;Kazuya Y;Noritaka M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2007,46:5202. |
| [36] | Rodríguez-Lugo R E;Trincado M;Grützmacher H .[J].ChemCatChem,2013,5:1079. |
| [37] | Xu L;Li N N;Peng H G;Wu P .[J].ChemCatChem,2013,5:2462. |
| [38] | Zhou, B.;Du, J.;Yang, Y.;Li, Y. .Rhodium(III)-catalyzed intermolecular direct amidation of aldehyde C-H bonds with N -chloroamines at room temperature[J].Organic letters,2013(12):2934-2937. |
| [39] | Ng, K.-H.;Zhou, Z.;Yu, W.-Y. .Rhodium(III)-catalyzed intermolecular direct amination of aromatic C-H bonds with N-chloroamines[J].Organic letters,2012(1):272-275. |
| [40] | Grohmann, C.;Wang, H.;Glorius, F. .Rh[III]-catalyzed direct C-H amination using N -chloroamines at room temperature[J].Organic letters,2012(2):656-659. |
| [41] | Song G Y;Wang F;Li X W .[J].CHEMICAL SOCIETY REVIEWS,2012,41:3651. |
| [42] | 甄文萃,杜正银,李兴伟.三价铑催化亚甲胺内盐与丙烯酰胺氧化合成三取代吡唑[J].催化学报,2013(04):679-683. |
| [43] | Zhen W C;Wang F;Zhao M;Du Z Y Li X W .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2012,51:11819. |
| [44] | Heitman LH;van Veldhoven JPD;Zweemer AM;Ye K;Brussee J;IJzerman AP .False positives in a reporter gene assay: Identification and synthesis of substituted N-pyridin-2-ylbenzamides as competitive inhibitors of firefly luciferase[J].Journal of Medicinal Chemistry,2008(15):4724-4729. |
| [45] | Kulkarni SS;Nightingale B;Dersch CM;Rothman RB;Newman AH .Design and synthesis of noncompetitive metabotropic glutamate receptor subtype 5 antagonists.[J].Bioorganic and Medicinal Chemistry Letters,2006(13):3371-3375. |
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