|
|
构建酰胺类化合物的新进展
|
Abstract:
酰胺键的形成是有机化学中最重要的反应之一。因为酰胺类广泛存在于现代药物和生物活性物质中，然而酰胺键的合成作为当代的挑战经常被忽视。早期合成酰胺的方法有着它们固有的局限性，反应简单快速、方法的普适性越来越受到人们的重视，开发新颖的形成酰胺键的化学方法势在必行。在合成酰胺键的许多方法中，利用催化方法来制备这类重要的官能团备受人们关注，其中金属催化与光催化反应的应用得到广泛关注。催化剂用于形成酰胺键已成为在关键领域中一些最新文献的亮点。醇、醛、羧酸作为底物和有机胺在各种条件下反应得到相应的酰胺。回顾并总结酰胺的合成方法有助于解决目前工艺中存有的问题。
The formation of amide bonds is one of the most important reactions in organic chemistry. Because amides are widely found in modern pharmaceuticals and bioactives, the synthesis of amide bonds is often overlooked as a contemporary challenge. The early methods of synthesizing amides have their inherent limitations, and the simple and rapid reaction and the universality of the method have attracted more and more attention, and it is imperative to develop novel chemical methods for the formation of amide bonds. Among the many methods for the synthesis of amide bonds, the use of catalytic methods to prepare these important functional groups has attracted much attention, among which the application of transition metal catalysis and photocatalytic reaction has received extensive attention. The use of catalysts for the formation of amide bonds has been the highlight of some of the latest literature in key areas. Alcohols, aldehydes, carboxylic acids and organic amines are reacted as substrates to obtain corresponding amides under various conditions. Reviewing and summarizing the synthesis methods of amides can help to solve the problems existing in the current process.
| [1] | Carey, J.S., Laffan, D., Thomson, C. and Williams, M.T. (2006) Analysis of the Reactions Used for the Preparation of Drug Candidate Molecules. Organic & Biomolecular Chemistry, 4, 2337-2347. https://doi.org/10.1039/b602413k |
| [2] | Ghose, A.K., Viswanadhan, V.N. and Wendoloski, J.J. (1998) A Knowledge-Based Approach in Designing Combinatorial or Medicinal Chemistry Libraries for Drug Discovery. 1. A Qualitative and Quantitative Characterization of Known Drug Databases. Journal of Combinatorial Chemistry, 1, 55-68. https://doi.org/10.1021/cc9800071 |
| [3] | Roughley, S.D. and Jordan, A.M. (2011) The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates. Journal of Medicinal Chemistry, 54, 3451-3479. https://doi.org/10.1021/jm200187y |
| [4] | Charville, H., Jackson, D.A., Hodges, G., Whiting, A. and Wilson, M.R. (2011) The Uncatalyzed Direct Amide Formation Reaction—Mechanism Studies and the Key Role of Carboxylic Acid H‐Bonding. European Journal of Organic Chemistry, 2011, 5981-5990. https://doi.org/10.1002/ejoc.201100714 |
| [5] | Perreux, L., Loupy, A. and Volatron, F. (2002) Solvent-Free Preparation of Amides from Acids and Primary Amines under Microwave Irradiation. Tetrahedron, 58, 2155-2162. https://doi.org/10.1016/s0040-4020(02)00085-6 |
| [6] | Lanigan, R.M. and Sheppard, T.D. (2013) Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation Reactions. European Journal of Organic Chemistry, 2013, 7453-7465. https://doi.org/10.1002/ejoc.201300573 |
| [7] | Lanigan, R.M. and Sheppard, T.D. (2013) Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation Reactions. European Journal of Organic Chemistry, 2013, 7453-7465. https://doi.org/10.1002/ejoc.201300573 |
| [8] | Han, S. and Kim, Y. (2004) Recent Development of Peptide Coupling Reagents in Organic Synthesis. Tetrahedron, 60, 2447-2467. https://doi.org/10.1016/j.tet.2004.01.020 |
| [9] | El-Faham, A. and Albericio, F. (2011) Peptide Coupling Reagents, More than a Letter Soup. Chemical Reviews, 111, 6557-6602. https://doi.org/10.1021/cr100048w |
| [10] | Dunetz, J.R., Magano, J. and Weisenburger, G.A. (2016) Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals. Organic Process Research & Development, 20, 140-177. https://doi.org/10.1021/op500305s |
| [11] | Valeur, E. and Bradley, M. (2009) Amide Bond Formation: Beyond the Myth of Coupling Reagents. Chemical Society Reviews, 38, 606-631. https://doi.org/10.1039/b701677h |
| [12] | Montalbetti, C.A.G.N. and Falque, V. (2005) Amide Bond Formation and Peptide Coupling. Tetrahedron, 61, 10827-10852. https://doi.org/10.1016/j.tet.2005.08.031 |
| [13] | de Figueiredo, R.M., Suppo, J. and Campagne, J. (2016) Nonclassical Routes for Amide Bond Formation. Chemical Reviews, 116, 12029-12122. https://doi.org/10.1021/acs.chemrev.6b00237 |
| [14] | Chandrudu, S., Simerska, P. and Toth, I. (2013) Chemical Methods for Peptide and Protein Production. Molecules, 18, 4373-4388. https://doi.org/10.3390/molecules18044373 |
| [15] | Constable, D.J.C., Dunn, P.J., Hayler, J.D., Humphrey, G.R., Leazer, Jr., J.L., Linderman, R.J., et al. (2007) Key Green Chemistry Research Areas—A Perspective from Pharmaceutical Manufacturers. Green Chem., 9, 411-420. https://doi.org/10.1039/b703488c |
| [16] | Zuo, Z., Ahneman, D.T., Chu, L., Terrett, J.A., Doyle, A.G. and MacMillan, D.W.C. (2014) Merging Photoredox with Nickel Catalysis: Coupling of α-Carboxyl Sp3-Carbons with Aryl Halides. Science, 345, 437-440. https://doi.org/10.1126/science.1255525 |
| [17] | Zuo, Z., Cong, H., Li, W., Choi, J., Fu, G.C. and MacMillan, D.W.C. (2016) Enantioselective Decarboxylative Arylation of Α-Amino Acids via the Merger of Photoredox and Nickel Catalysis. Journal of the American Chemical Society, 138, 1832-1835. https://doi.org/10.1021/jacs.5b13211 |
| [18] | Zhang, G., Zhou, S., Fu, L., Chen, P., Li, Y., Zou, J., et al. (2020) Asymmetric Coupling of Carbon‐Centered Radicals Adjacent to Nitrogen: Copper‐catalyzed Cyanation and Etherification of Enamides. Angewandte Chemie International Edition, 59, 20439-20444. https://doi.org/10.1002/anie.202008338 |
| [19] | Ji, C., Zhai, X., Fang, Q., Zhu, C., Han, J. and Xie, J. (2023) Photoinduced Activation of Alkyl Chlorides. Chemical Society Reviews, 52, 6120-6138. https://doi.org/10.1039/d3cs00110e |
| [20] | Fairbanks, B.D., Macdougall, L.J., Mavila, S., Sinha, J., Kirkpatrick, B.E., Anseth, K.S., et al. (2021) Photoclick Chemistry: A Bright Idea. Chemical Reviews, 121, 6915-6990. https://doi.org/10.1021/acs.chemrev.0c01212 |
| [21] | Romero, N.A. and Nicewicz, D.A. (2016) Organic Photoredox Catalysis. Chemical Reviews, 116, 10075-10166. https://doi.org/10.1021/acs.chemrev.6b00057 |
| [22] | Zhang, J. and Rueping, M. (2023) Metallaphotoredox Catalysis for Sp3 C-H Functionalizations through Hydrogen Atom Transfer (HAT). Chemical Society Reviews, 52, 4099-4120. https://doi.org/10.1039/d3cs00023k |
| [23] | Chen, C. and Hong, S.H. (2011) Oxidative Amide Synthesis Directly from Alcohols with Amines. Organic & Biomolecular Chemistry, 9, 20-26. https://doi.org/10.1039/c0ob00342e |
| [24] | Dobereiner, G.E. and Crabtree, R.H. (2009) Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis. Chemical Reviews, 110, 681-703. https://doi.org/10.1021/cr900202j |
| [25] | Zhang, Y., Chen, C., Ghosh, S.C., Li, Y. and Hong, S.H. (2010) Well-Defined N-Heterocyclic Carbene Based Ruthenium Catalysts for Direct Amide Synthesis from Alcohols and Amines. Organometallics, 29, 1374-1378. https://doi.org/10.1021/om901020h |
| [26] | Fujita, K., Takahashi, Y., Owaki, M., Yamamoto, K. and Yamaguchi, R. (2004) Synthesis of Five-, Six-, and Seven-Membered Ring Lactams by Cp*Rh Complex-Catalyzed Oxidative N-Heterocyclization of Amino Alcohols. Organic Letters, 6, 2785-2788. https://doi.org/10.1021/ol0489954 |
| [27] | Ghosh, S.C. and Hong, S.H. (2010) Simple RuCl3‐Catalyzed Amide Synthesis from Alcohols and Amines. European Journal of Organic Chemistry, 2010, 4266-4270. https://doi.org/10.1002/ejoc.201000362 |
| [28] | Chen, C. and Hong, S.H. (2012) Selective Catalytic Sp3 C-O Bond Cleavage with C-N Bond Formation in 3-Alkoxy-1-Propanols. Organic Letters, 14, 2992-2995. https://doi.org/10.1021/ol3009842 |
| [29] | Watson, A.J.A., Wakeham, R.J., Maxwell, A.C. and Williams, J.M.J. (2014) Ruthenium-Catalysed Oxidation of Alcohols to Amides Using a Hydrogen Acceptor. Tetrahedron, 70, 3683-3690. https://doi.org/10.1016/j.tet.2014.04.017 |
| [30] | Schley, N.D., Dobereiner, G.E. and Crabtree, R.H. (2011) Oxidative Synthesis of Amides and Pyrroles via Dehydrogenative Alcohol Oxidation by Ruthenium Diphosphine Diamine Complexes. Organometallics, 30, 4174-4179. https://doi.org/10.1021/om2004755 |
| [31] | Mielby, J., Riisager, A., Fristrup, P. and Kegnæs, S. (2013) Mechanistic Investigation of the One-Pot Formation of Amides by Oxidative Coupling of Alcohols with Amines in Methanol. Catalysis Today, 203, 211-216. https://doi.org/10.1016/j.cattod.2012.04.026 |
| [32] | Srimani, D., Balaraman, E., Hu, P., Ben‐David, Y. and Milstein, D. (2013) Formation of Tertiary Amides and Dihydrogen by Dehydrogenative Coupling of Primary Alcohols with Secondary Amines Catalyzed by Ruthenium Bipyridine‐based Pincer Complexes. Advanced Synthesis & Catalysis, 355, 2525-2530. https://doi.org/10.1002/adsc.201300620 |
| [33] | Gunanathan, C., Ben-David, Y. and Milstein, D. (2007) Direct Synthesis of Amides from Alcohols and Amines with Liberation of H 2. Science, 317, 790-792. https://doi.org/10.1126/science.1145295 |
| [34] | Muthaiah, S., Ghosh, S.C., Jee, J., Chen, C., Zhang, J. and Hong, S.H. (2010) Direct Amide Synthesis from Either Alcohols or Aldehydes with Amines: Activity of Ru(II) Hydride and Ru(0) Complexes. The Journal of Organic Chemistry, 75, 3002-3006. https://doi.org/10.1021/jo100254g |
| [35] | Zweifel, T., Naubron, J. and Grützmacher, H. (2008) Catalyzed Dehydrogenative Coupling of Primary Alcohols with Water, Methanol, or Amines. Angewandte Chemie International Edition, 48, 559-563. https://doi.org/10.1002/anie.200804757 |
| [36] | Ghosh, S.C., Ngiam, J.S.Y., Seayad, A.M., Tuan, D.T., Johannes, C.W. and Chen, A. (2013) Tandem Oxidative Amidation of Benzyl Alcohols with Amine Hydrochloride Salts Catalysed by Iron Nitrate. Tetrahedron Letters, 54, 4922-4925. https://doi.org/10.1016/j.tetlet.2013.07.005 |
| [37] | Zultanski, S.L., Zhao, J. and Stahl, S.S. (2016) Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines. Journal of the American Chemical Society, 138, 6416-6419. https://doi.org/10.1021/jacs.6b03931 |
| [38] | Wu, Z. and Hull, K.L. (2016) Rhodium-catalyzed Oxidative Amidation of Allylic Alcohols and Aldehydes: Effective Conversion of Amines and Anilines into Amides. Chemical Science, 7, 969-975. https://doi.org/10.1039/c5sc03103f |
| [39] | Kumar Achar, T. and Mal, P. (2015) Transformation of Contact‐Explosives Primary Amines and Iodine(III) into a Successful Chemical Reaction under Solvent‐Free Ball Milling Conditions. Advanced Synthesis & Catalysis, 357, 3977-3985. https://doi.org/10.1002/adsc.201500914 |
| [40] | Ishihara, K. and Yano, T. (2004) Synthesis of Carboxamides by LDA-Catalyzed Haller-Bauer and Cannizzaro Reactions. Organic Letters, 6, 1983-1986. https://doi.org/10.1021/ol0494459 |
| [41] | Mamaghani, M., Shirini, F., Sheykhan, M. and Mohsenimehr, M. (2015) Synthesis of a Copper(II) Complex Covalently Anchoring a (2-Iminomethyl)phenol Moiety Supported on HAp-Encapsulated-α-Fe2O3 as an Inorganic-Organic Hybrid Magnetic Nanocatalyst for the Synthesis of Primary and Secondary Amides. RSC Advances, 5, 44524-44529. https://doi.org/10.1039/c5ra03977k |
| [42] | Achar, T.K. and Mal, P. (2014) Radical-Induced Metal and Solvent-Free Cross-Coupling Using TBAI-TBHP: Oxidative Amidation of Aldehydes and Alcohols with n-Chloramines via C-H Activation. The Journal of Organic Chemistry, 80, 666-672. https://doi.org/10.1021/jo502464n |
| [43] | De Sarkar, S. and Studer, A. (2010) Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis. Organic Letters, 12, 1992-1995. https://doi.org/10.1021/ol1004643 |
| [44] | Vora, H.U. and Rovis, T. (2007) Nucleophilic Carbene and Hoat Relay Catalysis in an Amide Bond Coupling: An Orthogonal Peptide Bond Forming Reaction. Journal of the American Chemical Society, 129, 13796-13797. https://doi.org/10.1021/ja0764052 |
| [45] | Whittaker, A.M. and Dong, V.M. (2014) Nickel‐Catalyzed Dehydrogenative Cross‐Coupling: Direct Transformation of Aldehydes into Esters and Amides. Angewandte Chemie International Edition, 54, 1312-1315. https://doi.org/10.1002/anie.201410322 |
| [46] | Bode, J.W. and Sohn, S.S. (2007) N-heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines. Journal of the American Chemical Society, 129, 13798-13799. https://doi.org/10.1021/ja0768136 |
| [47] | Alanthadka, A. and Maheswari, C.U. (2015) N‐Heterocyclic Carbene‐Catalyzed Oxidative Amidation of Aldehydes with Amines. Advanced Synthesis & Catalysis, 357, 1199-1203. https://doi.org/10.1002/adsc.201400739 |
| [48] | Seo, S. and Marks, T.J. (2007) Mild Amidation of Aldehydes with Amines Mediated by Lanthanide Catalysts. Organic Letters, 10, 317-319. https://doi.org/10.1021/ol702788j |
| [49] | Ekoue-Kovi, K. and Wolf, C. (2007) Metal-Free One-Pot Oxidative Amination of Aldehydes to Amides. Organic Letters, 9, 3429-3432. https://doi.org/10.1021/ol7014626 |
| [50] | Ghosh, S.C., Ngiam, J.S.Y., Chai, C.L.L., Seayad, A.M., Dang, T.T. and Chen, A. (2012) Iron‐Catalyzed Efficient Synthesis of Amides from Aldehydes and Amine Hydrochloride Salts. Advanced Synthesis & Catalysis, 354, 1407-1412. https://doi.org/10.1002/adsc.201200020 |
| [51] | Yoo, W. and Li, C. (2006) Highly Efficient Oxidative Amidation of Aldehydes with Amine Hydrochloride Salts. Journal of the American Chemical Society, 128, 13064-13065. https://doi.org/10.1021/ja064315b |
| [52] | Qian, C., Zhang, X., Zhang, Y. and Shen, Q. (2010) Heterobimetallic Complexes of Lanthanide and Lithium Metals with Dianionic Guanidinate Ligands: Syntheses, Structures and Catalytic Activity for Amidation of Aldehydes with Amines. Journal of Organometallic Chemistry, 695, 747-752. https://doi.org/10.1016/j.jorganchem.2009.12.010 |
| [53] | Li, G., Kung, K.K. and Wong, M. (2012) Gold-Catalyzed Amide Synthesis from Aldehydes and Amines in Aqueous Medium. Chemical Communications, 48, 4112-4114. https://doi.org/10.1039/c2cc17689k |
| [54] | Ghosh, S.C., Ngiam, J.S.Y., Seayad, A.M., Tuan, D.T., Chai, C.L.L. and Chen, A. (2012) Copper-Catalyzed Oxidative Amidation of Aldehydes with Amine Salts: Synthesis of Primary, Secondary, and Tertiary Amides. The Journal of Organic Chemistry, 77, 8007-8015. https://doi.org/10.1021/jo301252c |
| [55] | Patel, O.P.S., Anand, D., Maurya, R.K. and Yadav, P.P. (2015) Copper-Catalyzed Highly Efficient Oxidative Amidation of Aldehydes with 2-Aminopyridines in an Aqueous Micellar System. Green Chemistry, 17, 3728-3732. https://doi.org/10.1039/c5gc00628g |
| [56] | Yang, S., Yan, H., Ren, X., Shi, X., Li, J., Wang, Y., et al. (2013) Copper-Catalyzed Dehydrogenative Reaction: Synthesis of Amide from Aldehydes and Aminopyridine. Tetrahedron, 69, 6431-6435. https://doi.org/10.1016/j.tet.2013.05.072 |
| [57] | Kuwano, S., Harada, S., Oriez, R. and Yamada, K. (2012) Chemoselective Conversion of α-Unbranched Aldehydes to Amides, Esters, and Carboxylic Acids by NHC-Catalysis. Chem. Commun., 48, 145-147. https://doi.org/10.1039/c1cc15539c |
| [58] | Wang, J., Li, J., Xu, F. and Shen, Q. (2009) Anionic Bridged Bis(amidinate) Lithium Lanthanide Complexes: Efficient Bimetallic Catalysts for Mild Amidation of Aldehydes with Amines. Advanced Synthesis & Catalysis, 351, 1363-1370. https://doi.org/10.1002/adsc.200800697 |
| [59] | Leow, D. (2014) Phenazinium Salt-Catalyzed Aerobic Oxidative Amidation of Aromatic Aldehydes. Organic Letters, 16, 5812-5815. https://doi.org/10.1021/ol5029354 |
| [60] | Gao, H., Guo, L., Zhu, Y., Yang, C. and Xia, W. (2023) Visible-Light-Induced Dehydrogenative Amidation of Aldehydes Enabled by Iron Salts. Chemical Communications, 59, 2771-2774. https://doi.org/10.1039/d2cc06507j |
| [61] | Kumar, V., Patel, S.K., Vyas, V., Kumar, D., Subramaniam Iyer, E.S. and Indra, A. (2024) Deciphering Charge Transfer Dynamics of a Lead Halide Perovskite-Nickel(II) Complex for Visible Light Photoredox C-N Coupling. Chemical Science, 15, 13218-13226. https://doi.org/10.1039/d4sc03023k |
| [62] | Al‐Zoubi, R.M., Marion, O. and Hall, D.G. (2008) Direct and Waste‐Free Amidations and Cycloadditions by Organocatalytic Activation of Carboxylic Acids at Room Temperature. Angewandte Chemie International Edition, 47, 2876-2879. https://doi.org/10.1002/anie.200705468 |
| [63] | Sakakura, A., Ohkubo, T., Yamashita, R., Akakura, M. and Ishihara, K. (2011) Brønsted Base-Assisted Boronic Acid Catalysis for the Dehydrative Intramolecular Condensation of Dicarboxylic Acids. Organic Letters, 13, 892-895. https://doi.org/10.1021/ol102926n |
| [64] | Nguyen, T.B., Sorres, J., Tran, M.Q., Ermolenko, L. and Al-Mourabit, A. (2012) Boric Acid: A Highly Efficient Catalyst for Transamidation of Carboxamides with Amines. Organic Letters, 14, 3202-3205. https://doi.org/10.1021/ol301308c |
| [65] | Yamashita, R., Sakakura, A. and Ishihara, K. (2013) Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative Amide Condensation of α-Hydroxycarboxylic Acids. Organic Letters, 15, 3654-3657. https://doi.org/10.1021/ol401537f |
| [66] | Cohen, I., Mishra, A.K., Parvari, G., Edrei, R., Dantus, M., Eichen, Y., et al. (2017) Sunlight Assisted Direct Amide Formation via a Charge-Transfer Complex. Chemical Communications, 53, 10128-10131. https://doi.org/10.1039/c7cc05300b |
| [67] | Mishra, A.K., Parvari, G., Santra, S.K., Bazylevich, A., Dorfman, O., Rahamim, J., et al. (2021) Solar and Visible Light Assisted Peptide Coupling. Angewandte Chemie International Edition, 60, 12406-12412. https://doi.org/10.1002/anie.202011510 |
| [68] | Chhatwal, A.R., Lomax, H.V., Blacker, A.J., Williams, J.M.J. and Marcé, P. (2020) Direct Synthesis of Amides from Nonactivated Carboxylic Acids Using Urea as Nitrogen Source and Mg(NO3)2 or Imidazole as Catalysts. Chemical Science, 11, 5808-5818. https://doi.org/10.1039/d0sc01317j |
