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分子中含O、S和N的杂环化合物,如呋喃、噻吩、吡咯和吲哚等及其衍生物是许多天然产物的活性成分,也是功能材料的重要构件.因此,开展杂环化合物简便高效的官能化反应的研究显得尤为重要.其中杂环化合物的烯丙基与苄基化反应是最具有吸引力的杂环官能团化反应之一.本文综述了杂环化合物的烯丙基化和苄基化反应的研究进展.

参考文献

[1] Cacchi S,Fabrizi G.Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions[J].Chem Rev,2005,105 (7):2873-2920.
[2] Eicher T,Hauptmann S.The Chemistry of Heterocycles[M].Wiley-VCH,Weinheim:Verlag GmbH & Co.KGaA,2003.
[3] Trost B M.The Atom Economy—A Search for Synthetic Efficiency[J].Science,1991,254:1471-1477.
[4] Trost B M.Selectivity:A Key to Synthetic Efficiency[J].Science,1983,219:245-250.
[5] Trost B M,Dong G.Total Synthesis of Bryostatin 16 Using Atom-Economical and Chemoselective Approaches[J].Nature,2008,456:485-488.
[6] Sanz R,Martínez A,Miguel D,et al.Brφnsted Acid-Catalyzed Nucleophilic Substitution of Alcohols[J].Adv Synth Catal,2006,348(14):1841-1845.
[7] Bras J L,Muzart J.Brφnsted-Acid-Catalyzed Coupling of Electron-Rich Arenes with Substituted Allylic and Secondary Benzylic Alcohols[J].Tetrahedron,2007,63 (13):7942-7948.
[8] Shirakawa S,Kobayashi S.Surfactant-Type Brφnsted Acid Catalyzed Dehydrative Nucleophilic Substitutions of Alcohols in Water[J].Org Lett,2007,9(2):311-314.
[9] Liu Y,Liu L,Wan Y,et al.Calix[n]arene Sulfonic Acids Bearing Pendant Aliphatic Chains as Recyclable Surfactant-Type Brφnsted Acid Catalysts for Allylic Alkylation with Allyl Alcohols in Water[J].Green Chem,2008,10 (6):635-640.
[10] Motokura K,Nakagiri N,Mizugaki T,et al.Nucleophilic Substitution Reactions of Alcohols with Use of Montmorillonite Catalysts as Solid Brφnsted Acids[J].J Org Chem,2007,72(16):6006-6015.
[11] McCubbin J A,Krokhin O V.Organocatalyzed Friedel-Crafts Arylation of Benzylic Alcohols[J].Tetrahedron Lett,2010,51 (18):2447-2449.
[12] Liu Z,Wang D,Wu Y,et al.Mild and Efficient Allylation of Indoles and Amides Using Amberlyst-15 as a Recyclable Heterogeneous Catalyst[J].Synth Commun,2012,42 (12):1813-1823.
[13] Malkov A V,Davis S L,Baxendale I R,et al.Molybdenum (Ⅱ)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics[J].J Org Chem,1999,64 (8):2751-2764.
[14] Yamamoto Y,Itonaga K.Versatile Friedel-Crafts-Type Alkylation of Benzene Derivatives Using a Molybdenum Complex/ortho-Chloranil Catalytic System[J].Chem Eur J,2008,14(34):10705-10715.
[15] Yang H,Fang L,Zhang M,et al.An Efficient Molybdenum (Ⅵ)-Catalyzed Direct Substitution of Allylic Alcohols with Nitrogen,Oxygen,and Carbon Nucleophiles[J].Eur J Org Chem,2009,(5):666-672.
[16] Yadav J S,Reddy B V S,Basak A K,et al.First Example of the C-Alkylation of Indoles with Baylis-Hillman Acetates[J].Tetrahedron Lett,2005,46 (4):639-641.
[17] Yadav J S,Reddy B V S,Aravind S,et al.InBr3 as a Versatile and Highly Efficient Catalyst for the Synthesis of 3-Allyl-and 3-Benzylindoles[J].Tetrahedron Lett,2007,48(35):6117-6120.
[18] Vicennati P,Cozzi P G.Facile Access to Optically Active Ferrocenyl Derivatives with Direct Substitution of the Hydroxy Group Catalyzed by Indium Tribromide[J].Eur J Org Chem,2007,(14):2248-2253.
[19] Yadav J S,Reddy B V S,Rao K V,et al.InCl3-Catalyzed Alkylation of Aromatic and Heteroaromatic Compounds with Cyclic Allylic Acetates[J].Synlett,2006,42 (20):3447-3450.
[20] Yasuda M,Somyo T,Baba A.Direct Carbon-Carbon Bond Formation from Alcohols and Active Methylenes,Alkoxyketones,or Indoles Catalyzed by Indium Trichloride[J].Angew Chem Int Ed,2006,45(5):793-796.
[21] Krause N,Winter C.Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes:A Powerful Access to Carbo-and Heterocycles[J].Chem Rev,2011,111 (3):1994-2009.
[22] Hashmi A S K.Gold-Catalyzed Organic Reactions[J].Chem Rev,2007,107(7):3180-3211.
[23] Georgy M,Boucard V,Campagne J.Gold (Ⅲ)-Catalyzed Nucleophilic Substitution of Propargylic Alcohols[J].J Am Chem Soc,2005,127(41):14180-14181.
[24] Liu J,Muth E,Florke U,et al.Alkylation of Arenes with Benzylic and Propargylic Alcohols-Classical versus Fancy Catalysts[J].Adv Synth Catal,2006,348(4/5):456-462.
[25] Mertins K,Lovel I,Kischel J,et al.Gold-Catalyzed Benzylation of Arenes and Heteroarenes[J].Adv Synth Catal,2006,348(6):691-695.
[26] Rao W,Chan P W H.Gold-catalysed Allylic Alkylation of Aromatic and Heteroaromatic Compounds with Allylic Alcohols[J].Org Biomol Chem,2008,6(13):2426-2433.
[27] Chen G,Xu Z,Chan S L,et al.Homogeneous Silver(Ⅰ) Salts and Heterogeneous Ag3 PW12O40-Catalyzed Intermolecular Allylation of Arenes with Allylic Alcohols[J].Synlett,2011,(18):2713-2718.
[28] Niggemann M,Meel M J.Calcium-Catalyzed Friedel-Crafts Alkylation at Room Temperature[J].Angew Chem Int Ed,2010,49(21):3684-3687.
[29] Jana U,Maiti S,Biswas S.An FeCl3-Catalyzed Highly C3-Selective Friedel-Crafts Alkylation of Indoles with Alcohols[J].Tetrahedron Lett,2007,48 (40):7160-7163.
[30] Wang B Q,Xiang S K,Sun Z P,et al.Benzylation of Arenes Through FeCl3-Catalyzed Friedel-Crafts Reaction via C-O Activation of Benzyl Ether[J].Tetrahedron Lett,2008,49 (27):4310-4312.
[31] Tsuji J,Takahashi H,Morikawa M.Organic Syntheses by Means of Noble Metal Compounds:ⅩⅦ.Reaction of π-Allylpalladium Chloride with Nucleophiles[J].Tetrahedron Lett,1965,6(49):4387-4388.
[32] Trost B M,Fullerton T J.New Synthetic Reactions.Allylic Alkylation[J].J Am Chem Soc,1973,95 (1):292-294.
[33] Trost B M,Van Vranken D L.Asymmetric Transition Metal-Catalyzed Allylic Alkylations[J].Chem Rev,1996,96(1):395-422.
[34] Billups W E,Erkes R S,Reed L E.Palladium Catalyzed Allylation of Indole[J].Synth Commun,1980,10(2):147-154.
[35] Bandini M,Melloni A,Umani-Ronchi A.New Versatile Pd-Catalyzed Alkylation of Indoles via Nucleophilic Allylic Substitution:Controlling the Regioselectivity[J].Org Lett,2004,6 (18):3199-3202.
[36] Kimura M,Futamata M,Mukai R,et al.Pd-Catalyzed C3-Selective Allylation of Indoles with Allyl Alcohols Promoted by Triethylborane[J].J Am Chem Soc,2005,127 (13):4592-4593.
[37] Ma S,Yu S,Peng Z,et al.Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted ElectronDeficient Alkenes[J].J Org Chem,2006,71 (26):9865-9868.
[38] Trost B M,Quancard J.Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes[J].J Am Chem Soc,2006,128(19):6314-6315.
[39] Bandini M,Melloni A,Piccinelli F,et al.Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines via Pd-Catalyzed Intramolecular Allylic Alkylation[J].J Am Chem Soc,2006,128(5):1424-1425.
[40] Cheung H Y,Yu W,Lam F L,et al.Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles by a New Class of Chiral Ferrocenyl P/S Ligands[J].Org Lett,2007,9 (21):4295-4298.
[41] Trost B M,Crawley M L.Asymmetric Transition-Metal-Catalyzed Allylic Alkylations:Applications in Total Synthesis[J].Chem Rev,2003,103 (8):2921-2943.
[42] Hoshi T,Sasaki K,Sato S,et al.Highly Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles Using Sulfur-MOP Ligand[J].Org Lett,2011,13(5):932-935.
[43] Liu Z,Cao Z,Du H.Highly Effective Chiral Phosphorus Amidite-Olefin Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions[J].Org Biomol Chem,2011,9(15):5369-5372.
[44] Cao Z,Liu Y,Liu Z,et al.Pd-Catalyzed Asymmetric Allylic Alkylation of Indoles and Pyrroles by Chiral Alkene-Phosphine Ligands[J].Org Lett,2011,13(9):2164-2167.
[45] Usui I,Schmidt S,Keller M,et al.Allylation of N-Heterocycles with Allylic Alcohols Employing Self-Assembling Palladium Phosphane Catalysts[J].Org Lett,2008,10 (6):1207-1210.
[46] Yuan F Q,Gao L X,Han F S.PdCl2-Catalyzed Efficient Allylation and Benzylation of Heteroarenes under Ligand,Base/Acid,and Additive-Free Conditions[J].Chem Commun,2011,47 (18):5289-5291.
[47] Yuan F Q,Sun F Y,Han F S.A Simple and Efficient Method for the Allylation of Heteroarenes Catalyzed by PdCl2[J].Tetrahedron,2012,68 (34):6837-6842.
[48] Onodera G,Imajima H,Yamanashi M,et al.Ruthenium-Catalyzed Allylation of Aromatic Compounds and Allylic Ether Formation[J].Organometallics,2004,23 (24):5841-5848.
[49] Zaitsev A B,Gruber S,Pregosin P S.Fast,Efficient Ru (Ⅳ)-catalysed Regioselective Allylation of Indoles Using Allyl Alcohol(without Additives) under Mild Conditions[J].Chem Commun,2007,(44):4692-4693.
[50] Zaitsev A B,Gruber S,Plüss P A,et al.Fast and Highly Regioselective Allylation of Indole and Pyrrole Compounds by Allyl Alcohols Using Ru-Sulfonate Catalysts[J].J Am Chem Soc,2008,130 (35):11604-11605.
[51] Sundararaju B,Achard M,Demerseman B,et al.Ruthenium (Ⅳ) Complexes Featuring P,O-Chelating Ligands:Regioselective Substitution Directly from Allylic Alcohols[J].Angew Chem Int Ed,2010,49(15):2782-2785.
[52] Yadav J S,Reddy B V S,Muralikrishna Reddy P,et al.Zinc-Mediated Barbier Reactions of Pyrrole and Indoles:A New Method for the Alkylation of Pyrrole and Indoles[J].Tetrahedron Lett,2002,43 (29):5185-5187.
[53] Prajapati D,Gohain M,Gogoi B J.Novel Gallium-Mediated C3-Allylation of Indoles and Pyrroles in Aqueous Media Promoted by Bu4NBr[J].Tetrahedron Lett,2006,47(21):3535-3539.
[54] Liu Z,Liu L,Shafiq Z,et al.Iodine-Catalyzed Allylation and Propargylation of Indoles with Allylic and Propargylic Acetates[J].Tetrahedron Lett,2007,48(23):3963-3967.
[55] Westermaier M,Mayr H.Electrophilic Allylations and Benzylations of Indoles in Neutral Aqueous or Alcoholic Solutions[J].Org Lett,2006,8(21):4791-4794.
[56] Cozzi P G,Zoli L.A Rational Approach towards the Nucleophilic Substitutions of Alcohols "on Water"[J].Angew Chem Int Ed,2008,47 (22):4162-4166.
[57] Hirashita T,Kuwahara S,Okochi S,et al.Direct Benzylation and Allylic Alkylation in High-Temperature Water without Added Catalysts[J].Tetrahedron Lett,2010,51 (14):1847-1851.
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