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·1414·                            精细化工   FINE CHEMICALS                                 第 38 卷

                        表 7   酰胺化反应底物拓展                            formylation of amines and transamidation of amides under solvent-free
                Table 7    Substrate expansion of amidation reaction   conditions[J]. RSC Advances, 2015, 5(98): 80441-80449.
                                                               [6]   MANE R S,  BHANAGE B M.  Carbonylative tertiary amide
             编号    有机酸       有机胺    产物       结构      收率/%          synthesis from aryl iodides and tertiary amines via oxidant-free C—
                                                                   N bond cleavage catalyzed by palladium(Ⅱ) chloride in polyethylene
              1                       2a               96          glycol/water[J]. Advanced Synthesis  & Catalysis, 2017, 359(15):
                                                                   2621-2629.
                                                               [7]   KHEDKAR M V, KHAN S R, SAWANT D N, et al. Palladium on
              2                       2b               86
                                                                   carbon: An efficient, heterogeneous and reusable catalytic system for
                                                                   carbonylative synthesis of N-substituted phthalimides[J]. Advanced
                                                                   Synthesis & Catalysis, 2011, 353(18): 3415-3422.
              3                       2c               89
                                                               [8]   SAWANT D N, WAGH Y S, BHATTE K D, et al. Carbon monoxide-free
                                                                   one-step synthesis of isoindole-1,3-diones by cycloaminocarbonylation
              4                       2d               92          of  o-haloarenes using formamides[J]. European Journal  of Organic
                                                                   Chemistry, 2011, 2011(33): 6719-6724.
                                                               [9]   MATSUOKA A, ISOGAWA T, MORIOKA Y,  et al. Hydration of
              5                       2e               90          nitriles to amides by a chitin-supported ruthenium catalyst[J]. RSC
                                                                   Advances, 2015, 5(16): 12152-12160.
                                                               [10]  LEE D S, AMARA Z, POLIAKOFF M, et al. Investigating scale-up
              6                      2f                80          and further applications of DABAL-Me3 promoted amide synthesis[J].

                                                                   Organic Process Research & Development, 2015, 19(7): 831-840.
                                                               [11]  MCPHERSON C G, CALDWELL N, JAMIESON C, et al. Amidation
              7                      2g                79
                                                                   of unactivated ester derivatives mediated by trifluoroethanol[J].
                                                                   Organic & Biomolecular Chemistry, 2017, 15(16): 3507-3518.
              8                      2h                77      [12]  LENSTRA D C, NGUYEN D T, MECINOVIC J. Zirconium-catalyzed
                                                                   direct amide bond formation between carboxylic esters and amines[J].
                                                                   Tetrahedron, 2015, 71(34): 5547-5553.
              9                      2i                83      [13]  TILLACK A,  RUDLOFF I, BELLER M. Catalytic  amination of
                                                                   aldehydes to amides[J]. European Journal of Organic Chemistry,

                                                                   2001, 2001(3): 523-528.
                                                               [14]  GUNANATHAN C, BEN-DAVID Y, MILSTEIN D. Direct synthesis
            3    结论                                                of amides from alcohols and amines with liberation of H 2[J]. Science,
                                                                   2007, 317(5839): 790-792.
                                                               [15]  LANIGAN R M, STARKOV P, SHEPPARD T D. Direct synthesis of
                 以 NbCl 5 和离子液体[BMIm]Br 作为共催化剂,                    amides from  carboxylic acids and amines using B(OCH 2CF 3) 3[J].
            催化有机酸和有机胺一步法合成酰胺类化合物,得                                 Journal of Organic Chemistry, 2013, 78(9): 4512-4523.
                                                               [16]  LU Y, WANG K, ISHIHARA K. Design of boronic acid-base complexes
            出如下结论:                                                 as reusable homogeneous catalysts in dehydrative condensations
                (1)以苯甲酸和苄胺的酰胺化反应作为模型反                              between carboxylic acids and amines[J]. Asian Journal of Organic
                                                                   Chemistry, 2017, 6(9): 1191-1194.
            应,获得了最优反应条件:有机酸 2.0 mmol,有机                        [17]  LEGGIO A, BAGALA J, BELSITO E L, et al. Formation of amides:
            胺 2.0 mmol,NbCl 5  0.16 mmol,1-甲基-3-丁基咪唑               One-pot condensation of carboxylic acids and amines  mediated by
                                                                   TiCl 4[J]. Chemistry Central Journal, 2017, 11: 87.
            溴化物 0.3 mmol,4A M.S. 200 mg,甲苯 4 mL,反
                                                               [18]  NERY M,  RIBEIRO R, LOPES C,  et al. Niobium pentachloride
            应温度 110  ℃,反应时间 24 h。在最优反应条件下,                         promoted conversion of carboxylic acids to carboxamides: Synthesis
            合成了 9 个酰胺类产物,收率可达 77%~96%。                             of the 4aryl1,2,3,4-tetrahydroisoquinoline alkaloid structures[J].
                                                                   Synthesis, 2003, (2): 272-276.
                (2)本文所用合成酰胺类化合物的方法无需惰                          [19]  RANU B  C,  BANERJEE S. Ionic liquid as catalyst  and reaction
            性气体保护,方法操作简单,产物易于纯化,为具                                 medium.  The dramatic influence of a task-specific ionic liquid,
                                                                   [bmIm]OH, in  michael addition of active methylene  compounds to
            有重要应用价值的酰胺类化合物的合成提供了一种                                 conjugated ketones, carboxylic esters, and  nitriles[J]. Organic
            高效、快速方便的方法,具有广阔的应用前景。                                  Letters, 2005, 7(14): 3049-3052.
                                                               [20]  SUN Z (孙哲), HE J M (何金梅), QU M N (屈孟男), et al. Progress
            参考文献:                                                  of cooperative catalysis in organic synthesis[J]. Chinese  Journal of
                                                                   Organic Chemistry (有机化学), 2015, 35(6): 1250-1259.
            [1]   FISCHBACH M A, WALSH  C T.  Assembly-line enzymology for   [21]  MITTAL N, NISOLA G M, CHUNG W J. Facile catalytic dehydration
                 polyketide and nonribosomal peptide antibiotics:  Logic, machinery,   of fructose to 5-hydroxymethylfurfural by niobium pentachloride[J].
                 and mechanisms[J]. Chemical Reviews, 2006, 106(8): 3468-3496.   Tetrahedron Letters, 2012, 53(25): 3149-3155.
            [2]   NORDSTR M L U, VOGT H, MADSEN R. Amide synthesis from   [22] ZHU L (朱林), HAN W(韩威), LI W S (李文松). Highly selective
                 alcohols and amines by the extrusion of dihydrogen[J]. Journal of the   hydrolyzation of cyclohexyl acetate over HZSM-5 assisted by [BMIm]Br
                 American Chemical Society, 2008, 130(52): 17672-17673.   ionic liquid[J]. CIESC Journal(化工学报), 2020, 71(4): 1609-1617.
            [3]   ZHANG X F, CHEN X F, ZHAO W Y, et al. GlcNAc conjugated   [23]  GUGLIELMERO L, MEZZETTA A, GUAZZELLI L, et al. Systematic
                 atorvastatin with enhanced water solubility and cellular internalization[J].   synthesis and properties evaluation of dicationic ionic liquids, and a
                 Bioconjugate Chemistry, 2017, 28(8): 2109-2113.   glance into a potential new field[J]. Frontiers in Chemistry, 2018,
            [4]   STEPANOVS D, JURE M, GOSTEVA M,  et al. Crystal structures   6:612.
                 and physicochemical properties  of  diltiazem base and its acetylsalicylate,   [24]  ALGHATTA  A,  WILTON-ELY J D E  T, HALLETT J P. Efficient
                 nicotinate and l-malate salts[J]. CrystEngComm, 2016, 18(7): 1235-1241.   formation  of  2, 5-diformylfuran in ionic liquids at high substrate
            [5]   YEDAGE S L, D'SILVA D S, BHANAGE B M. MnO 2 catalyzed   loadings and low oxygen pressure with separation through sublimation[J].
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