液相贝克曼重排反应催化剂研究进展
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摘要
贝克曼重排(Backmann rearrangement)反应是制备酰胺常用方法之一,其中液相贝克曼重排反应因其反应条件较温和应用广泛,本文对离子液体、无机酸、有机酸、路易斯酸及其他反应型催化对贝克曼重排反应影响研究情况做了较为详尽综述。
Backman rearrangement is one of the common way preparating amide, the liquid phase method has been widely used because of its mild reaction conditions. Several kinds of catalyst such as ionic liquid, inorganic acid, organic acid, Lewis acid and Mukaiyama reagent were introduced in detail.
Backman rearrangement is one of the common way preparating amide, the liquid phase method has been widely used because of its mild reaction conditions. Several kinds of catalyst such as ionic liquid, inorganic acid, organic acid, Lewis acid and Mukaiyama reagent were introduced in detail.
引文
[1]荣国斌,袁履冰,王全瑞,等.高等有机化学[M].上海:华东理工大学出版社,2007:457.
[2]Donaruma L G,Heldt W Z.The Beckmann rearrangement[J].Org.Reactions,1960,11:1-156.
[3]Chu Y,Ji P,Yi X,et al.Strong or weak acid,which is more efficient for Beckmann rearrangement reaction over solid acid catalysts[J].Catalysis Science&Technology,2015,5:3675.
[4]Pi H J,Dong J D,An N,et al.Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using Ts Cl[J].Tetrahedron,2009,65:7790.
[5]Izumi Y,Sato S,Urabe K.Vapor-phase Beckmann rearrangement of cyclohexanone oxime over boria-hydroxyapatite catalyst[J].Chemistry Letters,1983,12:1649.
[6]Conesa T D,Luque R,Campelo J M,et al.Gas-phase Beckmann rearrangement of cyclododecanone oxime on Al,B-MCM-41 mesoporous materials[J].Journal of materials science,2009,44:6741.
[7]Hao F,Zhong J,Liu P L,et al.Preparation of mesoporous Si O2-Al2O3supported Co or Mn catalysts and their catalytic properties in cyclohexane nitrosation toε-caprolactam[J].Journal of Molecular Catalysis A:Chemical,2011,351:210.
[8]贾金锋.液相贝克曼重排合成ε-己内酰胺研究[D].郑州:郑州大学,2015.
[9]黄碧纯,黄仲涛.离子液体的研究开发及其在催化反应中的应用[J].工业催化,2003,11:1.
[10]Wasserscheid P,Keim W.Ionic liquids—new“solutions”for transition metal catalysis[J].Angewandte Chemie International Edition,2000,39:3772.
[11]Peng J,Deng Y.Catalytic Beckmann rearrangement of ketoximes in ionic liquids[J].Tetrahedron Letters,2001,42:403.
[12]Kore R,Srivastava R.A simple,eco-friendly,and recyclable bi-functional acidic ionic liquid catalysts for Beckmann rearrangement[J].Journal of Molecular Catalysis A:Chemical,2013,376:90.
[13]王洪林,张文媛.在负载离子液体的MCM-48上的环己酮肟重排[J].云南大学学报(自然科学版),2008,30(2):180.
[14]Ren R X,Zueva L D,Ou W.Formation ofε-caprolactam via catalytic Beckmann rearrangement using P2O5in ionic liquids[J].Tetrahedron Letters,2001,42:8441.
[15]Li Z,Ding R,Lu Z,et al.Silica sulfate as a recyclable and efficient catalyst for Beckmann rearrangement under microwave irradiation[J].Journal of Molecular Catalysis A:Chemical,2006,250:100.
[16]程庆彦,姬亚宁,王延吉.微波辐射促进P2O5催化液相贝克曼重排制己内酰胺[J].石油学报(石油加工),2011,27:393.
[17]Sato H,Yoshioka H,Izumi Y.Homogeneous liquid-phase Beckmann rearrangement of oxime catalyzed by phosphorous pentaoxide and accelerated by fluorine-containing strong acid[J].Journal of Molecular Catalysis A:Chemical,1999,149:25.
[18]Marziano N C,Ronchin L,Tortato C,et al.Catalyzed Beckmann rearrangement of cyclohexanone oxime in heterogeneous liquid/solid system:Part 1:Batch and continuous operation with supported acid catalysts[J].Journal of Molecular Catalysis A:Chemical,2007,277:221.
[19]Ngamcharussrivichai C,Wu P,Tatsumi T.Catalytically active and selective centers for production of?-caprolactam through liquid phase Beckmann rearrangement over H-USY catalyst[J].Applied Catalysis A:General,2005,288:158.
[20]Xiao L,Xia C,Chen J.p-Toluenesulfonic acid mediated zinc chloride:highly effective catalyst for the Beckmann rearrangement[J].Tetrahedron Letters,2007,48:7218.
[21]张风雷,章亚东.温和催化液相重排制备ε-己内酰胺[J].精细化工,2013,30:1073.
[22]You K,Mao L,Yin D,et al.Beckmann rearrangement of cyclohexanone oxime toε-caprolactam catalyzed by sulfonic acid resin in DMSO[J].Catalysis Communications,2008,9:1521.
[23]De Luca L,Giacomelli G,Porcheddu A.Beckmann rearrangement of oximes under very mild conditions[J].The Journal of organic chemistry,2002,67:6272.
[24]Hashimoto M,Obora Y,Sakaguchi S,et al.Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst[J].The Journal of organic chemistry,2008,73:2894.
[25]Narahari S R,Reguri B R,Mukkanti K.Beckmann rearrangement of oximes using pivaloyl chloride/DMF complex[J].Tetrahedron letters,2011,52:4888.
[26]Liu L F,Liu H,Pi H J,et al.Facile Al Cl3-Promoted Catalytic Beckmann Rearrangement of Ketoximes[J].Synthetic Communications,2011,41:553.
[27]Ghiaci M,Imanzadeh G H.A facile Beckmann rearrangement of oximes w ith Al Cl3in the solid state[J].Synthetic communications,1998,28:2275.
[28]Mahajan S,Sharma B,Kapoor K K.A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by Fe Cl3·6H2O in presence of hydroxylamine hydrochloride[J].Tetrahedron Letters,2015,56:1915.
[29]Mahajan S,Sharma B,Kapoor K K.A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by Fe Cl3·6H2O in presence of hydroxylamine hydrochloride[J].Tetrahedron Letters,2015,56:1915.
[30]Pai S G,Bajpai A R,Deshpande A B,et al.Beckmann rearrangement of substituted diaryl ketoximes using Fe Cl3impregnated montmorillonite K10[J].Synthetic communications,1997,27:379.
[31]Thakur A J,Boruah A,Prajapati D,et al.Microwave induced bismuth trichloride catalysed Beckmann rearrangement of oximes[J].Synthetic Communications,2000,30:2105.
[32]Loupy A,Régnier S.Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes[J].Tetrahedron letters,1999,40:6221.
[33]Furuya Y,Ishihara K,Yamamoto H.Cyanuric chloride as a mild and active Beckmann rearrangement catalyst[J].Journal of the American Chemical Society,2005,127:11240.
[34]Li J T,Meng X T,Yin Y.Efficient pr ocedure for Beckmann rearrangement of ketoximes catalyzed by sulfamic acid/zinc chloride[J].Synthetic CommunicationsR,2010,40:1445.
[35]Wang B,Gu Y,Luo C,et al.Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement,a green process to produce amides from ketoximes without waste[J].Tetrahedron letters,2004,45:3369.
[36]Ramalingan C,Park Y T.Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile[J].The Journal of organic chemistry,2007,72:4536.
[37]Kanta De S.Ru Cl3catalyzed facile conversion of arylalkyl ketoximes to amides[J].Synthetic communications,2004,34:3431.
[38]Arisawa M,Yamaguchi M.Rhodium-catalyzed Beckmann rearrangement[J].Organic letters,2001,3:311.
[39]Kikugawa Y,Tsuji C,Miyazawa E,et al.A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition[J].Tetrahedron Letters,2001,42:2337.
[40]Torisawa Y,Nishi T,Minamikawa J.Continuing efforts on the improvement of Beckmann rearrangement of indanone oxime[J].Bioorganic&medicinal chemistry letters,2007,17:448.
[41]Azadi R,Shams L.The Highly efficient Beckmann rearrangement of ketoximes to amides by using Mukaiyama reagent under mild conditions[J].Letters in Organic Chemistry,2017,14:141.
[2]Donaruma L G,Heldt W Z.The Beckmann rearrangement[J].Org.Reactions,1960,11:1-156.
[3]Chu Y,Ji P,Yi X,et al.Strong or weak acid,which is more efficient for Beckmann rearrangement reaction over solid acid catalysts[J].Catalysis Science&Technology,2015,5:3675.
[4]Pi H J,Dong J D,An N,et al.Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using Ts Cl[J].Tetrahedron,2009,65:7790.
[5]Izumi Y,Sato S,Urabe K.Vapor-phase Beckmann rearrangement of cyclohexanone oxime over boria-hydroxyapatite catalyst[J].Chemistry Letters,1983,12:1649.
[6]Conesa T D,Luque R,Campelo J M,et al.Gas-phase Beckmann rearrangement of cyclododecanone oxime on Al,B-MCM-41 mesoporous materials[J].Journal of materials science,2009,44:6741.
[7]Hao F,Zhong J,Liu P L,et al.Preparation of mesoporous Si O2-Al2O3supported Co or Mn catalysts and their catalytic properties in cyclohexane nitrosation toε-caprolactam[J].Journal of Molecular Catalysis A:Chemical,2011,351:210.
[8]贾金锋.液相贝克曼重排合成ε-己内酰胺研究[D].郑州:郑州大学,2015.
[9]黄碧纯,黄仲涛.离子液体的研究开发及其在催化反应中的应用[J].工业催化,2003,11:1.
[10]Wasserscheid P,Keim W.Ionic liquids—new“solutions”for transition metal catalysis[J].Angewandte Chemie International Edition,2000,39:3772.
[11]Peng J,Deng Y.Catalytic Beckmann rearrangement of ketoximes in ionic liquids[J].Tetrahedron Letters,2001,42:403.
[12]Kore R,Srivastava R.A simple,eco-friendly,and recyclable bi-functional acidic ionic liquid catalysts for Beckmann rearrangement[J].Journal of Molecular Catalysis A:Chemical,2013,376:90.
[13]王洪林,张文媛.在负载离子液体的MCM-48上的环己酮肟重排[J].云南大学学报(自然科学版),2008,30(2):180.
[14]Ren R X,Zueva L D,Ou W.Formation ofε-caprolactam via catalytic Beckmann rearrangement using P2O5in ionic liquids[J].Tetrahedron Letters,2001,42:8441.
[15]Li Z,Ding R,Lu Z,et al.Silica sulfate as a recyclable and efficient catalyst for Beckmann rearrangement under microwave irradiation[J].Journal of Molecular Catalysis A:Chemical,2006,250:100.
[16]程庆彦,姬亚宁,王延吉.微波辐射促进P2O5催化液相贝克曼重排制己内酰胺[J].石油学报(石油加工),2011,27:393.
[17]Sato H,Yoshioka H,Izumi Y.Homogeneous liquid-phase Beckmann rearrangement of oxime catalyzed by phosphorous pentaoxide and accelerated by fluorine-containing strong acid[J].Journal of Molecular Catalysis A:Chemical,1999,149:25.
[18]Marziano N C,Ronchin L,Tortato C,et al.Catalyzed Beckmann rearrangement of cyclohexanone oxime in heterogeneous liquid/solid system:Part 1:Batch and continuous operation with supported acid catalysts[J].Journal of Molecular Catalysis A:Chemical,2007,277:221.
[19]Ngamcharussrivichai C,Wu P,Tatsumi T.Catalytically active and selective centers for production of?-caprolactam through liquid phase Beckmann rearrangement over H-USY catalyst[J].Applied Catalysis A:General,2005,288:158.
[20]Xiao L,Xia C,Chen J.p-Toluenesulfonic acid mediated zinc chloride:highly effective catalyst for the Beckmann rearrangement[J].Tetrahedron Letters,2007,48:7218.
[21]张风雷,章亚东.温和催化液相重排制备ε-己内酰胺[J].精细化工,2013,30:1073.
[22]You K,Mao L,Yin D,et al.Beckmann rearrangement of cyclohexanone oxime toε-caprolactam catalyzed by sulfonic acid resin in DMSO[J].Catalysis Communications,2008,9:1521.
[23]De Luca L,Giacomelli G,Porcheddu A.Beckmann rearrangement of oximes under very mild conditions[J].The Journal of organic chemistry,2002,67:6272.
[24]Hashimoto M,Obora Y,Sakaguchi S,et al.Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst[J].The Journal of organic chemistry,2008,73:2894.
[25]Narahari S R,Reguri B R,Mukkanti K.Beckmann rearrangement of oximes using pivaloyl chloride/DMF complex[J].Tetrahedron letters,2011,52:4888.
[26]Liu L F,Liu H,Pi H J,et al.Facile Al Cl3-Promoted Catalytic Beckmann Rearrangement of Ketoximes[J].Synthetic Communications,2011,41:553.
[27]Ghiaci M,Imanzadeh G H.A facile Beckmann rearrangement of oximes w ith Al Cl3in the solid state[J].Synthetic communications,1998,28:2275.
[28]Mahajan S,Sharma B,Kapoor K K.A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by Fe Cl3·6H2O in presence of hydroxylamine hydrochloride[J].Tetrahedron Letters,2015,56:1915.
[29]Mahajan S,Sharma B,Kapoor K K.A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by Fe Cl3·6H2O in presence of hydroxylamine hydrochloride[J].Tetrahedron Letters,2015,56:1915.
[30]Pai S G,Bajpai A R,Deshpande A B,et al.Beckmann rearrangement of substituted diaryl ketoximes using Fe Cl3impregnated montmorillonite K10[J].Synthetic communications,1997,27:379.
[31]Thakur A J,Boruah A,Prajapati D,et al.Microwave induced bismuth trichloride catalysed Beckmann rearrangement of oximes[J].Synthetic Communications,2000,30:2105.
[32]Loupy A,Régnier S.Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes[J].Tetrahedron letters,1999,40:6221.
[33]Furuya Y,Ishihara K,Yamamoto H.Cyanuric chloride as a mild and active Beckmann rearrangement catalyst[J].Journal of the American Chemical Society,2005,127:11240.
[34]Li J T,Meng X T,Yin Y.Efficient pr ocedure for Beckmann rearrangement of ketoximes catalyzed by sulfamic acid/zinc chloride[J].Synthetic CommunicationsR,2010,40:1445.
[35]Wang B,Gu Y,Luo C,et al.Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement,a green process to produce amides from ketoximes without waste[J].Tetrahedron letters,2004,45:3369.
[36]Ramalingan C,Park Y T.Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile[J].The Journal of organic chemistry,2007,72:4536.
[37]Kanta De S.Ru Cl3catalyzed facile conversion of arylalkyl ketoximes to amides[J].Synthetic communications,2004,34:3431.
[38]Arisawa M,Yamaguchi M.Rhodium-catalyzed Beckmann rearrangement[J].Organic letters,2001,3:311.
[39]Kikugawa Y,Tsuji C,Miyazawa E,et al.A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition[J].Tetrahedron Letters,2001,42:2337.
[40]Torisawa Y,Nishi T,Minamikawa J.Continuing efforts on the improvement of Beckmann rearrangement of indanone oxime[J].Bioorganic&medicinal chemistry letters,2007,17:448.
[41]Azadi R,Shams L.The Highly efficient Beckmann rearrangement of ketoximes to amides by using Mukaiyama reagent under mild conditions[J].Letters in Organic Chemistry,2017,14:141.