Nickel-Catalyzed Amide Bond Formation from Methyl Esters.
作者： Taoufik Ben Halima , Jeanne Masson-Makdissi , Stephen G. Newman
关键词:
摘要: Despite being one of the most important and frequently run chemical reactions, synthesis amide bonds is accomplished primarily by wasteful methods that proceed stoichiometric activation starting materials. We report a nickel-catalyzed procedure can enable diverse amides to be synthesized from abundant methyl ester materials, producing only volatile alcohol as waste product. In contrast acid- base-mediated amidations, reaction proposed neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.
sci-hub.se 参考文章(52)
Danny C. Lenstra, D. Thao Nguyen, Jasmin Mecinović, Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines Tetrahedron. ,vol. 71, pp. 5547- 5553 ,(2015) , 10.1016/J.TET.2015.06.066
Nicole A. LaBerge, Jennifer A. Love, Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids European Journal of Organic Chemistry. ,vol. 2015, pp. 5546- 5553 ,(2015) , 10.1002/EJOC.201500630
Liana Hie, Noah F. Fine Nathel, Tejas K. Shah, Emma L. Baker, Xin Hong, Yun-Fang Yang, Peng Liu, K. N. Houk, Neil K. Garg, Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds Nature. ,vol. 524, pp. 79- 83 ,(2015) , 10.1038/NATURE14615
Nicola Caldwell, Craig Jamieson, Iain Simpson, Allan J. B. Watson, Catalytic amidation of unactivated ester derivatives mediated by trifluoroethanol. Chemical Communications. ,vol. 51, pp. 9495- 9498 ,(2015) , 10.1039/C5CC02895G
Chong Han, Jonathan P. Lee, Emil Lobkovsky, John A. Porco, Catalytic Ester−Amide Exchange Using Group (IV) Metal Alkoxide−Activator Complexes Journal of the American Chemical Society. ,vol. 127, pp. 10039- 10044 ,(2005) , 10.1021/JA0527976
Juan de M. Muñoz, Jesús Alcázar, Antonio de la Hoz, Ángel Díaz-Ortiz, Sergio-A. Alonso de Diego, Preparation of amides mediated by isopropylmagnesium chloride under continuous flow conditions Green Chemistry. ,vol. 14, pp. 1335- 1341 ,(2012) , 10.1039/C2GC35037H
Hiroyuki Morimoto, Risa Fujiwara, Yuhei Shimizu, Kazuhiro Morisaki, Takashi Ohshima, Lanthanum(III) triflate catalyzed direct amidation of esters. Organic Letters. ,vol. 16, pp. 2018- 2021 ,(2014) , 10.1021/OL500593V
Simon E. Ward, Mark Harries, Laura Aldegheri, Nigel E. Austin, Stuart Ballantine, Elisa Ballini, Daniel M. Bradley, Benjamin D. Bax, Brian P. Clarke, Andrew J. Harris, Stephen A. Harrison, Rosemary A. Melarange, Claudette Mookherjee, Julie Mosley, Gianni Dal Negro, Beatrice Oliosi, Kathrine J. Smith, Kevin M. Thewlis, Patrick M. Woollard, Shahnaz P. Yusaf, Integration of lead optimization with crystallography for a membrane-bound ion channel target: discovery of a new class of AMPA receptor positive allosteric modulators. Journal of Medicinal Chemistry. ,vol. 54, pp. 78- 94 ,(2011) , 10.1021/JM100679E
Mohammad Movassaghi, Michael A. Schmidt, N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols. Organic Letters. ,vol. 7, pp. 2453- 2456 ,(2005) , 10.1021/OL050773Y
Jorge C.S. Costa, Josiane S. Neves, Marcus V.N. de Souza, Rodrigo A. Siqueira, Nelilma C. Romeiro, Nubia Boechat, Patrícia M.R.e Silva, Marco A. Martins, Synthesis and antispasmodic activity of lidocaine derivatives endowed with reduced local anesthetic action Bioorganic & Medicinal Chemistry Letters. ,vol. 18, pp. 1162- 1166 ,(2008) , 10.1016/J.BMCL.2007.11.122