非膦钯催化Suzuki偶联反应
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摘要
考察了非膦体系Pd/哌嗪衍生物在超声波辅助下催化Suzuki偶联反应的催化活性。在以碳酸钾为碱助剂,甲醇作溶剂,超声波辅助,30℃水浴中,催化剂Pd/哌嗪衍生物(1.0 mol%)能在短时间内催化芳溴衍生物和活化芳氯衍生物与苯硼酸偶联,以优秀的收率得到相应的偶联产物。
The catalytic activities of phosphine-free palladium/piperazine derivatives for Suzuki cross-coupling reaction assisted with ultrasound were investigated. The coupled products of aryl bromides and aryl chlorides derivatives coupled with phenylboronic acid were obtained with an excellent amount, which were catalyzed by phosphine-free palladium/piperazine derivatives(1.0 mol%) in shorter reaction time under 30℃, using K_2CO_3 as a base, methanol as a solvent and piperazine derivative as ligand.
The catalytic activities of phosphine-free palladium/piperazine derivatives for Suzuki cross-coupling reaction assisted with ultrasound were investigated. The coupled products of aryl bromides and aryl chlorides derivatives coupled with phenylboronic acid were obtained with an excellent amount, which were catalyzed by phosphine-free palladium/piperazine derivatives(1.0 mol%) in shorter reaction time under 30℃, using K_2CO_3 as a base, methanol as a solvent and piperazine derivative as ligand.
引文
[1]Miyaura N,Yamada K,Suzuki A.A new stereospecific cross-coupling by the palladium-catalyzed reaction of1-alkenylboranes with 1-alkenyl or 1-alkynyl halides[J].Tetrahedron Letters,1979,20(36):3437-3440.
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[3]Neau E,Raspo I,Escandell J,et al.Handbook of organopalladium chemistry for organic synthesis M].Handbook of organopalladium chemistry for organic synthesis.Wiley-Interscience,2002:3031-3126.
[4]Molnár A.Efficient,selective,and recyclable palladium catalysts in carbon-carbon coupling reactions[J].Chem.Rev.,2011,111(3):2251-2320.
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[7]Rühling A,Rakers L,Glorius F.Long alkyl chain NHC palladium complexes for the amination and hydrodehalogenation of aryl chlorides in lipophilic media[J].Chemcatchem,2016,9(4):714-714.
[8]Bo Z,Qiu J,Li J,Schluter A D.Synthesis of Aryl/Alkyl building blocks for dendrimer and hyperbranched polymer synthesis[J].Org.Lett.,2004,6(5):667-669.
[9]李程鹏,罗妙,彭元怀,等.荧光可调控的二噻吩乙烯-萘酰亚胺光致变色化合物的合成及性能研究[J].井冈山大学学报:自然科学版,2016,37(4):21-25.
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[11]Yuan Y,Men H,Lee C.Total synthesis of kendomycin:a cacro-c-glycosidation approach[J].J.Am.Chem.Soc.,2004,126(45):14720-14721.
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[13]Fuwa H,Kainuma N,Tachibana K,et al.Total synthesis of(-)-gambierol[J].J.Am.Chem.Soc.,2002,124(50):14983-14992.
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[15]Kandathil V,Fahlman B D,Sasidhar B S,et al.A convenient,efficient and reusable N-heterocyclic carbene-palladium(ii)based catalyst supported on magnetite for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions[J].New J.Chem.,2017,41(17):9531-9545.
[16]Grasa G A,Hillier A C,Nolan S P.Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system[J].Org.Lett.,2001,3(7):1077-1080.
[17]Felpin F X,Lory C,Sow H,et al.Practical and efficient entry to isoflavones by Pd(0)/C-mediated SuzukiMiyaura reaction.Total synthesis of geranylated isoflavones[J].Tetrahedron,2007,63(14):3010-3016.
[18]Gade L H,Bellemin-Laponnaz S.Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis[J].Top.Curr.Chem.,2007,2007(21):117-157.
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[21]Chemler S R,Trauner D,Danishefsky S J.The B-alkyl Suzuki-Miyaura cross-coupling reaction:Development,mechanistic study,and applications in natural product synthesis[J].Angew.Chem.Int.Ed.,2001,40(24):4544-4568.
[22]Konno T,Daitoh T,Noiri A,et al.A highly regio-and stereoselective carbocupration of fluoroalkylated internal alkynes:A short total synthesis of the antiestrogenic drug panomifene[J].Org.Lett.,2004,6(6):933-936.
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[24]Zhou Z G,Zhao Y,Zhen H Y,et al.Poly(ethylene glycol)-and glucopyranoside-substituted N-heterocyclic carbene precursors for the synthesis of arylfluorene derivatives using efficient palladium-catalyzed aqueous Suzuki reaction[J].Appl.Organomet.Chem.,2016,30(11):924-931.
[25]Shi J-C,Zhou Z G,Zheng S,et al.Carbohydrate-based phosphines as supporting ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction[J].Tetrahedron Lett.,2014,55(18):2904-2907.
[26]Zhou Z G,Qiu J B,Xie L F,et al.Synthesis of chiral imidazolium salts from a carbohydrate and their application in Pd-catalyzed Suzuki-Miyaura reaction[J].Catal.Lett.,2014,144(11):1911-1918.
[27]Zhou Z G,Shi J-C,Hu Q S,et al.Suzuki cross-coupling reactions of aryl chlorides using[Pd(COD)Cl2]/piperazine derivative under microwave conditions[J].Appl.Organomet.Chem.,2011,25(8):616-619.
[28]许瑞波,杨雯雯,万蓓蓓.连云港山楂叶黄酮的超声提取及体外活性研究[J].井冈山大学学报:自然科学版,2016,37(6):24-29.
[29]Uozumi Y,Matsuura Y,Arakawa T,et al.Asymmetric Suzuki-Miyaura coupling in water with a chiral palladium catalyst supported on an amphiphilic resin[J].Angew.Chem.Int.Ed.,2009,48(15);2708-2710.
[30]张宏,王新平,杨鹏宇,等.钯-二茂铁配合物催化的Suzuki-Miyaura偶联反应[J].应用化学,2007,24(9):986-990.
[31]Xue J,Zhou Z G,Peng J,et al.PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water[J].Transition Met.Chem.,2014,39(2):221-224.
[32]Imanaka Y,Nakao K,Maeda Y,et al.Sugar-incorporated chelating bis-N-heterocyclic carbene palladium complexes.Synthesis,structures,and catalytic ability for Suzuki-Miyaura cross-coupling reactions in water[J].Bull.Chem.Soc.Jpn.,2017,90(9):1050-1057.
[2]Suzuki A.Carbon-carbon bonding made easy[J].Chem.Commun.,2005,10(38):4759-4763.
[3]Neau E,Raspo I,Escandell J,et al.Handbook of organopalladium chemistry for organic synthesis M].Handbook of organopalladium chemistry for organic synthesis.Wiley-Interscience,2002:3031-3126.
[4]Molnár A.Efficient,selective,and recyclable palladium catalysts in carbon-carbon coupling reactions[J].Chem.Rev.,2011,111(3):2251-2320.
[5]Diederich F,De Meijere A.Metal-catalyzed cross-coupling reactions[M].2nd ed.Wiley-VCH:Weinheim,2004.
[6]Peris E.Smart N-heterocyclic carbene ligands in catalysis[J].Chem.Rev.,2017.DOI:10.1021/acs.chemrev.6b00695.
[7]Rühling A,Rakers L,Glorius F.Long alkyl chain NHC palladium complexes for the amination and hydrodehalogenation of aryl chlorides in lipophilic media[J].Chemcatchem,2016,9(4):714-714.
[8]Bo Z,Qiu J,Li J,Schluter A D.Synthesis of Aryl/Alkyl building blocks for dendrimer and hyperbranched polymer synthesis[J].Org.Lett.,2004,6(5):667-669.
[9]李程鹏,罗妙,彭元怀,等.荧光可调控的二噻吩乙烯-萘酰亚胺光致变色化合物的合成及性能研究[J].井冈山大学学报:自然科学版,2016,37(4):21-25.
[10]Lin S,Yang Z-Q,Kwok,et al.Total synthesis of TMC-95A and-B via a new reaction leading to z-enamides.some preliminary findings as to SAR[J].J.Am.Chem.Soc.,2004,126(20):6347-6355.
[11]Yuan Y,Men H,Lee C.Total synthesis of kendomycin:a cacro-c-glycosidation approach[J].J.Am.Chem.Soc.,2004,126(45):14720-14721.
[12]Lee S M,Yoon H J,Kim J H,et al.Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction[J].Pure Appl.Chem.,2007,79(9):1553-1559.
[13]Fuwa H,Kainuma N,Tachibana K,et al.Total synthesis of(-)-gambierol[J].J.Am.Chem.Soc.,2002,124(50):14983-14992.
[14]Mandal A K.Stereocontrolled total synthesis of(-)-ebelactone A[J].Org.Lett.,2002,4(12);2043-2045.
[15]Kandathil V,Fahlman B D,Sasidhar B S,et al.A convenient,efficient and reusable N-heterocyclic carbene-palladium(ii)based catalyst supported on magnetite for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions[J].New J.Chem.,2017,41(17):9531-9545.
[16]Grasa G A,Hillier A C,Nolan S P.Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system[J].Org.Lett.,2001,3(7):1077-1080.
[17]Felpin F X,Lory C,Sow H,et al.Practical and efficient entry to isoflavones by Pd(0)/C-mediated SuzukiMiyaura reaction.Total synthesis of geranylated isoflavones[J].Tetrahedron,2007,63(14):3010-3016.
[18]Gade L H,Bellemin-Laponnaz S.Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis[J].Top.Curr.Chem.,2007,2007(21):117-157.
[19]林进,吕仁庆.咪唑基离子液体与小分子相互作用的理论研究[J].井冈山大学学报:自然科学版,2013,34(1):39-46.
[20]Bellina F,Carpita A,Rossi R.Palladium catalysts for the Suzuki cross-coupling reaction:An overview of recent advances[J].Synthesis,2004,2004(15):2419-2440.
[21]Chemler S R,Trauner D,Danishefsky S J.The B-alkyl Suzuki-Miyaura cross-coupling reaction:Development,mechanistic study,and applications in natural product synthesis[J].Angew.Chem.Int.Ed.,2001,40(24):4544-4568.
[22]Konno T,Daitoh T,Noiri A,et al.A highly regio-and stereoselective carbocupration of fluoroalkylated internal alkynes:A short total synthesis of the antiestrogenic drug panomifene[J].Org.Lett.,2004,6(6):933-936.
[23]Shi J-C,Yang P Y,Tong Q S,et al.Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands[J].Dalton Trans.,2008,2008(7):938-945.
[24]Zhou Z G,Zhao Y,Zhen H Y,et al.Poly(ethylene glycol)-and glucopyranoside-substituted N-heterocyclic carbene precursors for the synthesis of arylfluorene derivatives using efficient palladium-catalyzed aqueous Suzuki reaction[J].Appl.Organomet.Chem.,2016,30(11):924-931.
[25]Shi J-C,Zhou Z G,Zheng S,et al.Carbohydrate-based phosphines as supporting ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction[J].Tetrahedron Lett.,2014,55(18):2904-2907.
[26]Zhou Z G,Qiu J B,Xie L F,et al.Synthesis of chiral imidazolium salts from a carbohydrate and their application in Pd-catalyzed Suzuki-Miyaura reaction[J].Catal.Lett.,2014,144(11):1911-1918.
[27]Zhou Z G,Shi J-C,Hu Q S,et al.Suzuki cross-coupling reactions of aryl chlorides using[Pd(COD)Cl2]/piperazine derivative under microwave conditions[J].Appl.Organomet.Chem.,2011,25(8):616-619.
[28]许瑞波,杨雯雯,万蓓蓓.连云港山楂叶黄酮的超声提取及体外活性研究[J].井冈山大学学报:自然科学版,2016,37(6):24-29.
[29]Uozumi Y,Matsuura Y,Arakawa T,et al.Asymmetric Suzuki-Miyaura coupling in water with a chiral palladium catalyst supported on an amphiphilic resin[J].Angew.Chem.Int.Ed.,2009,48(15);2708-2710.
[30]张宏,王新平,杨鹏宇,等.钯-二茂铁配合物催化的Suzuki-Miyaura偶联反应[J].应用化学,2007,24(9):986-990.
[31]Xue J,Zhou Z G,Peng J,et al.PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water[J].Transition Met.Chem.,2014,39(2):221-224.
[32]Imanaka Y,Nakao K,Maeda Y,et al.Sugar-incorporated chelating bis-N-heterocyclic carbene palladium complexes.Synthesis,structures,and catalytic ability for Suzuki-Miyaura cross-coupling reactions in water[J].Bull.Chem.Soc.Jpn.,2017,90(9):1050-1057.