Polycondensation via Complex-Catalyzed Carbon-Heteroatom Bond Formation

遷移金属触媒を用いた炭素-窒素結合形成反応を重縮合反応に応用することで,ポリアニリン類縁体やトリアリールアミン骨格を有する高分子を簡便に得ることができる.種々の条件の中でも,Pd と組合せる配位子が重合の効率に強く影響を及ぼすため,目的とする高分子の構造に合わせて適切な配位子を選択することが重要である.これまでの検討から,二級アミン部位を有するポリアニリン類縁体の合成においては BINAP が適しており,三級アミンであるトリアリールアミン骨格を主鎖に有する高分子の合成においては PtBu3 が最適であることを見いだしている.一方で,炭素-リン結合形成反応も重縮合反応に応用することができ,主鎖にキレート型のリン配位子を導入した高分子を合成することができる.この高分子に Pd を導入することで薗頭-萩原反応などを進行させる担持触媒となり,再沈殿によって回収と再利用が可能であることを明らかにしている.

[1]  T. Kanbara,et al.  Synthesis and Metal-like Luster of Novel Polyaniline Analogs Containing Azobenzene Unit , 2010 .

[2]  Kai A. I. Zhang,et al.  Conjugated polymers containing diketopyrrolopyrrole units in the main chain , 2010, Beilstein journal of organic chemistry.

[3]  Takakazu Yamamoto Synthesis of π-Conjugated Polymers by Organometallic Polycondensation , 2010 .

[4]  T. Tsutsui,et al.  Synthesis and Carrier Transport Properties of Triarylamine-based Amorphous Polymers for Organic Field-effect Transistors , 2009 .

[5]  T. Kanbara,et al.  Regioregulated Syntheses of Poly(aminopyridine)s by Pd-catalyzed Amination Reaction. , 2009, Macromolecular rapid communications.

[6]  M. Schäfer,et al.  Luminescent and Ionochromic Polyiminofluorene with Conjugated Terpyridine Substituent Groups , 2009 .

[7]  Kai A. I. Zhang,et al.  Purple red and luminescent polyiminoarylenes containing the 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) chromophore , 2009 .

[8]  K. Ogino,et al.  Preparation of diblock copolymer based on poly(4-n-butyltriphenylamine) via palladium coupling polymerization , 2009 .

[9]  M. Turner,et al.  Triarylamine polymers by microwave-assisted polycondensation for use in organic field-effect transistors† , 2008 .

[10]  M. Turner,et al.  Synthesis of Polytriarylamines via Microwave-Assisted Palladium-Catalysed Amination , 2007 .

[11]  B. Lucht,et al.  Poly-p-phenylene phosphine/polyaniline alternating copolymers: electronic delocalization through phosphorus. , 2005, Journal of the American Chemical Society.

[12]  M. Thelakkat,et al.  Synthesis and Characterization of Poly(triarylamine)s Containing Isothianaphthene Moieties , 2004 .

[13]  J. Hartwig Palladium‐Catalyzed Amination of Aryl Halides and Related Reactions , 2003 .

[14]  T. Meyer,et al.  o,p-Polyaniline: A New Form of a Classic Conducting Polymer , 2003 .

[15]  T. Michinobu,et al.  m-Phenylene-linked aromatic poly(aminium cationic radical)s: persistent high-spin organic polyradicals. , 2003, Organic letters.

[16]  M. Kakimoto,et al.  Synthesis and Properties of Hyperbranched Poly(triphenylamine)s Prepared by Palladium Catalyzed C–N Coupling Reaction , 2002 .

[17]  K. Oyaizu,et al.  Palladium‐catalyzed synthesis of oligo(methylthio)aniline and conversion to polyacene‐type electrolytes bearing phenothiazinium repeating units , 2002 .

[18]  B. Lucht,et al.  Transition metal mediated routes to poly(arylphosphine)s: investigation of novel phosphorus containing conjugated polymers , 2002 .

[19]  L. Do,et al.  Synthesis of novel fluorene-based poly(iminoarylene)s and their application to buffer layer in organic light-emitting diodes , 2002 .

[20]  E. Tsuchida,et al.  Synthesis of Novel Ladder Polymer Electrolytes Bridged by Sulfonio and Imino Groups , 2001 .

[21]  S. Buchwald,et al.  Efficient Synthesis of Well-Defined, High Molecular Weight, and Processible Polyanilines under Mild Conditions via Palladium-Catalyzed Amination , 2000 .

[22]  T. Kanbara,et al.  Palladium-catalyzed polycondensation of diiodobenzenes with 1,3-bis(phenylphosphino)propane and preparation of polymer transition-metal complexes , 2000 .

[23]  J. Hartwig,et al.  PALLADIUM-CATALYZED SYNTHESIS OF PURE, REGIODEFINED POLYMERIC TRIARYLAMINES , 1999 .

[24]  T. Kanbara,et al.  Preparation of Soluble Poly(iminoarylene)s by Palladium-Catalyzed Polycondensation of Aryl Dibromides with Aryl Primary Diamines , 1999 .

[25]  T. Kanbara,et al.  Preparation of New Polymers Containing an Azobenzene Group in the Side Chain by Palladium-Catalyzed Polymer Reaction and Polycondensation and Characterization of the Polymers , 1998 .

[26]  T. Kanbara,et al.  Preparation of Photocatalytically Active Polyamine and Polyamide Containing Acridine Group in the Main Chain by Palladium-catalyzed Polycondensation , 1998 .

[27]  T. Meyer,et al.  Linear and Hyperbranched m-Polyaniline: Synthesis of Polymers for the Study of Magnetism in Organic Systems , 1998 .

[28]  Yamamoto Toshihide,et al.  Palladium-catalyzed synthesis of triarylamines from aryl halides and diarylamines , 1998 .

[29]  J. Hartwig,et al.  Regiodefined Poly(N-arylaniline)s and Donor−Acceptor Copolymers via Palladium-Mediated Amination Chemistry , 1998 .

[30]  M. Nishiyama,et al.  Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst , 1998 .

[31]  T. Kanbara,et al.  Preparation of Poly(arylenediamine)s by Palladium-Catalyzed Polycondensation of Aryl Dibromides with Secondary Diamines , 1998 .

[32]  T. Kanbara,et al.  Preparation of Poly(imino-1,3-phenylene) and Its Related Polymer by Palladium-catalyzed Polycondensation , 1997 .

[33]  T. Kanbara,et al.  Preparation of Novel Poly(aryleneamine)s by Palladium Complex Catalyzed Polycondensation of Dibromobenzenes with Diamines , 1996 .

[34]  John P. Wolfe,et al.  An Improved Catalyst System for Aromatic Carbon−Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates , 1996 .

[35]  S. Buchwald,et al.  A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines , 1995 .

[36]  J. Hartwig,et al.  Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents , 1995 .

[37]  M. Kosugi,,et al.  PALLADIUM-CATALYZED AROMATIC AMINATION OF ARYL BROMIDES WITH N,N-DI-ETHYLAMINO-TRIBUTYLTIN , 1983 .