Title:
金属用のリガンドおよびそれらに基づいて改善された金属触媒法
Document Type and Number:
Japanese Patent JP5758844
Kind Code:
B2
Abstract:
One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject processes provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.
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Inventors:
Stefan Butchwold
David W Old
John P. Wolf
Michael paracchi
Ken Kamikawa
Andrew Chifi
Joseph P. Sadighi
Robert a singer
Jens Ahman
David W Old
John P. Wolf
Michael paracchi
Ken Kamikawa
Andrew Chifi
Joseph P. Sadighi
Robert a singer
Jens Ahman
Application Number:
JP2012111579A
Publication Date:
August 05, 2015
Filing Date:
May 15, 2012
Export Citation:
Assignee:
MASSACHUSETTS INSTITUTE OF TECHNOLOGY
International Classes:
C07F9/50; C07C1/26; C07C17/26; C07C41/14; C07C41/16; C07C43/20; C07C45/68; C07C45/71; C07C49/213; C07C49/233; C07C49/395; C07C49/403; C07C67/31; C07C205/04; C07C205/06; C07C209/06; C07C209/10; C07C209/14; C07C209/18; C07C211/45; C07C211/54; C07C211/59; C07C213/02; C07C213/08; C07C217/56; C07C221/00; C07C225/12; C07C225/22; C07C227/08; C07C227/18; C07C231/12; C07C249/02; C07C249/16; C07C251/16; C07C251/24; C07C251/86; C07C253/30; C07C255/58; C07D209/08; C07D209/10; C07D209/12; C07D209/14; C07D209/18; C07D213/50; C07D213/72; C07D213/74; C07D295/02; C07D295/023; C07D295/033; C07D295/08; C07D295/096; C07D295/112; C07D295/13; C07D295/14; C07D295/155; C07D307/33; C07D317/22; C07D317/26; C07D317/66; C07D333/08; C07D333/36; C07D333/66; C07D401/04; C07D401/10; C07F7/18; C07F9/48; C07F9/572; C07F9/653; C07F9/6547; C07F9/6571; C07F15/00; C07C211/48; C07C211/55; C07C217/40; C07C217/84; C07C217/92; C07C229/36; C07C229/60; C07C233/07; C07C235/46; C07C255/33; C07C255/50; C07C255/54; C07C255/56
Domestic Patent References:
| JP2001501954A | ||||
| JP5017491A | ||||
| JP7149777A | ||||
| JP7330786A | ||||
| JP9235289A | ||||
| JP9040684A | ||||
| JP9031084A |
Other References:
John P. Wolf, Seble Wagaw, Stephen L. Buchwald,An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complex as Key Intermediates,Journal of the American Chemical Society,米国,ACS Publications,1996年 7月31日,vol.118, No.30,p.7215-7216
Suk Young Cho, Masakatsu Shibasaki,Synthesis and Evaluation of a New Chiral Ligand: 2-diphenylarsino-2'-diphenylphoshino-1,1'-binaphthy (BINAPAs),Tetrahedron Letters,NL,Elsevier Science,1998年 3月26日,vol.39, No.13,p.1773-1776
Michael Palucki, John P. Wolfe, Stephen L. Buchwald,Palladium-Catalyzed Intermolecular Carbon-Oxygen Bond Formation: A New Synthesis of Aryl Ethers,Journal of the American Chemical Society,米国,ACS Publications,1997年 4月 9日,vol.119, No.14,p.3395-3396
Michael Palucki, John P. Wolfe, Stephen L. Buchwald,Synthesis of Oxygen Heterocycles via a Palladium-Catalyzed C-O Bond-Forming Reaction,Journal of the American Chemical Society,米国,ACS Publications,1996年10月23日,vol.118, No.42,p.10333-10334
Jahyo Kang, Sung Hoon Yu, Joo In Kim, Hyung Geun Cho,Catalytic Asymmetric Allylic Alkylation with A Novel P-S Bidentate Ligand,Bulletin of the Korean Chemical Society,KR,1995年 5月20日,vol.16, No.5,p.439-443
Serafino Gladiali, Antonio Dore, Davide Fabbri,Novel Heterobidentate Ligands for Asymmetric Catalysis: Synthesis and Rhodium-catalysed Reactions of S-Alkyl (R)-2-Diphenylphosphino-1,1'-binaphthyl-2'-thiol,Tetrahedron Asymmetry,NL,Elsevier Science,1994年 7月,vol.5, No.7,p.1143-1146
Tvo Crameri, Joseph Foricher, Michelangelo Scalone, Rudolf Schmid,Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calc,Tetrahedron: Asymmetry,NL,Elsevier Science,1997年,Vol.8, No.21,p.3617-3623
Tamio Hayashi,Asymmetric Hydrosilylation of Olefins Catalyzed by MOP-Palladium Complexes,Acta Chemica Scandinavica,デンマーク,The Chemical Societies in Denmark, Finland, Norway, and Sweden,1996年 3月,vol.50, No.3,p.259-266
Serafino Gladiali, Antonio Dore, Davide Fabbri,Synthesis, Crystal Structure, Dynamic Behavior and Reactivity of Dinaphtho[2,1-b:1',2'-d]phospholes and Related Atropisomeric Phosphacyclic Derivatives,Journal of Organic Chemistry,米国,ACS Publications,1994年10月21日,Vol.59, No.21,p.6363-6371
Tetsurtaro Hattori, Jun'ichi Sakamoto, Noriyuki Hayashizaka, Sotaro Miyano,Nucleophilic Aromatic Substitution Reactions of 1-Methoxy-2-(diphenylphosphinyl)naphtalene with C-, N-, and O-Nucleophiles: Facile Synthesis of Diphenyl(1-substituted-2-naphthyl)phosphines,Synthesis,ドイツ,Thieme Chemistry,1994年 2月,No.2,p.199-202
Simona Bronco, Giambattista Consiglio,Regio- and stereoregular copolymerisation of propene with carbon monoxide catalysed by palladium containing atropisomeric diphosphine ligands,Macromolecular Chemistry and Physics,ドイツ,Wiley-VCH,1996年 1月,vol.197, No.1,p.355-365
Wolfgang A. Herrmann, Christoph Brossmer, Claus-Peter Reisinger, Thomas H. Riermeier, Karl Ofere, Matthias Beller,Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides,Chemistry - A European Journal,ドイツ,Wiley-VCH,1997年 8月,vol.3, No.8,p.1357-1364
D. F. Gill, B. E. Mann, B. L. Shaw,Transition Metal-Carbon Bonds. Part XXXIII. International Metallations of Secondary and Tertiary Carbon Atoms by Platinum(II) and Palladium(II),Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1973年 3月,No.3,p.270-278
H. David Empsall, Peter N. heys, Bernard L. Shaw,Complexes of Platinum and Palladium with Tertiary Dimethoxyphenylphosphines: Attempts to Effect O- or C-Metallation,Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1978年 3月,No.3,p.257-262
Christopher E. Jones, Bernard L. Shaw, Brian L. Turtle,O- and C-Metallation of 2-Alkoxyphenylphosphines by Platinum(II),Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1974年 6月,No.9,p.992-999
Thomas Langer, Jorg Janssen, Gunter Helmchen,Catalytic Asymmetric Hydrosilylation of Ketones Using Rhodium-(I)-Complexes of Chiral Phosphinooxazoline Ligands,Tetrahedron Asymmetry,NL,Elsevier Science,1996年 6月 1日,vol.7, No.6,p.1599-1602
Toshihide Yamamoto, Masakazu Nishiyama, Yasuyuki Koie,Palladium-Catalyzed Synthesis of Triarylamines from Aryl Halides and Diarylamines,Tetrahedron Letters,NL,Elsevier Science,1998年 4月16日,vol.39, No.7,p.2367-2370
Masakazu Nishiyama, Toshihide Yamamoto, Yasuyuki Koie,Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine inder a Palladium Tri-tert-butylphosphine Catalyst,Tetrahedron Letters,NL,Elsevier Science,1998年 2月12日,vol.39, No.7,p.617-620
Nagavelli Prabhakae Reddy, Masato Tanaka,Palladium-Catalyzed Amination of Aryl Chlorides,Tetrahedron Letters,NL,Elsevier Science,1997年 7月 7日,vol.38, No.27,p.4807-4810
Attila Aranyos, David W. Old, Ayumu Kiyomori, John P. Wolfe, Joseph P. Sadighi, Stephen L. Buchwald,Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers,Journal of the American Chemical Society,米国,ACS Publications,1999年 5月12日,vol.121, No.18,p.4369-4378
Stepan Vyskocil, Martin Smrcina, Vladimir Hanus, Miroslav Polasek, Pavel Kocovsky,Derivatives of 2-Amino-2'-diphenylphosphino-1,1'-binaphthyl (MAP) and Their Application in Asymmetric Palladium(0)-Catalyzed Allylic Substitution,Journal of Organic Chemistry,英国,Royal Society of Chemistry,1998年10月30日,Vol.63, No.22,p.7738-7748
Kuiling Ding, Yang Wang, Hongying Yun, Jinxia Liu, Yangjie Wu, Masahiro Terada, Yasutaka Okubo, Koichi Mikami,Highly Effect and Practical Optical Resolution of 2-Amino-2'-hydroxy-1,1'-binaphthyl by Molecular Complexation with N-Benzylcinchonidium Chloride: A Direct Transformation to Binaphthyl Amino Phosphine,Chemistry - A European Journal,ドイツ,Wiley-VCH,1999年 6月 4日,vol.5, No.6,p.1734-1737
David W. Old, John P. Wolfe, Stephen L. Buchwald,A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Tmperature Suzuki Couplings and Amination of Unactivated Aryl CHlorides,Journal of the American Chemical Society,米国,ACS Publications,1998年 9月23日,vol.120, No.37,p.9722-9723
Blake C. Hamann, John F. Hartwig,Sterically Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and CHlorides, and the First Amination of Aryl Tosylates,Journal of the American Chemical Society,米国,ACS Publications,1998年 7月29日,vol.120, No.29,p.7369-7370
John P. Wolfe, Robert A. Singer, Bryant H. Yang, Stephen L. Buchwald,Highly Active Palladium Catalysts for Suzuki Coupling Reactions,Journal of the American Chemical Society,米国,ACS Publications,1999年10月20日,vol.121, No.41,p.9550-9561
John P. Wolfe, Stephen L. Buchwald,A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides,Angewandte Chemie International Edition,ドイツ,Wiley-VCH,1999年 8月12日,vol.38, No.16,p.2413-2416
Suk Young Cho, Masakatsu Shibasaki,Synthesis and Evaluation of a New Chiral Ligand: 2-diphenylarsino-2'-diphenylphoshino-1,1'-binaphthy (BINAPAs),Tetrahedron Letters,NL,Elsevier Science,1998年 3月26日,vol.39, No.13,p.1773-1776
Michael Palucki, John P. Wolfe, Stephen L. Buchwald,Palladium-Catalyzed Intermolecular Carbon-Oxygen Bond Formation: A New Synthesis of Aryl Ethers,Journal of the American Chemical Society,米国,ACS Publications,1997年 4月 9日,vol.119, No.14,p.3395-3396
Michael Palucki, John P. Wolfe, Stephen L. Buchwald,Synthesis of Oxygen Heterocycles via a Palladium-Catalyzed C-O Bond-Forming Reaction,Journal of the American Chemical Society,米国,ACS Publications,1996年10月23日,vol.118, No.42,p.10333-10334
Jahyo Kang, Sung Hoon Yu, Joo In Kim, Hyung Geun Cho,Catalytic Asymmetric Allylic Alkylation with A Novel P-S Bidentate Ligand,Bulletin of the Korean Chemical Society,KR,1995年 5月20日,vol.16, No.5,p.439-443
Serafino Gladiali, Antonio Dore, Davide Fabbri,Novel Heterobidentate Ligands for Asymmetric Catalysis: Synthesis and Rhodium-catalysed Reactions of S-Alkyl (R)-2-Diphenylphosphino-1,1'-binaphthyl-2'-thiol,Tetrahedron Asymmetry,NL,Elsevier Science,1994年 7月,vol.5, No.7,p.1143-1146
Tvo Crameri, Joseph Foricher, Michelangelo Scalone, Rudolf Schmid,Practical synthesis of (S)-2-(4-fluorophenyl)-3-methylbutanoic acid, key building block for the calc,Tetrahedron: Asymmetry,NL,Elsevier Science,1997年,Vol.8, No.21,p.3617-3623
Tamio Hayashi,Asymmetric Hydrosilylation of Olefins Catalyzed by MOP-Palladium Complexes,Acta Chemica Scandinavica,デンマーク,The Chemical Societies in Denmark, Finland, Norway, and Sweden,1996年 3月,vol.50, No.3,p.259-266
Serafino Gladiali, Antonio Dore, Davide Fabbri,Synthesis, Crystal Structure, Dynamic Behavior and Reactivity of Dinaphtho[2,1-b:1',2'-d]phospholes and Related Atropisomeric Phosphacyclic Derivatives,Journal of Organic Chemistry,米国,ACS Publications,1994年10月21日,Vol.59, No.21,p.6363-6371
Tetsurtaro Hattori, Jun'ichi Sakamoto, Noriyuki Hayashizaka, Sotaro Miyano,Nucleophilic Aromatic Substitution Reactions of 1-Methoxy-2-(diphenylphosphinyl)naphtalene with C-, N-, and O-Nucleophiles: Facile Synthesis of Diphenyl(1-substituted-2-naphthyl)phosphines,Synthesis,ドイツ,Thieme Chemistry,1994年 2月,No.2,p.199-202
Simona Bronco, Giambattista Consiglio,Regio- and stereoregular copolymerisation of propene with carbon monoxide catalysed by palladium containing atropisomeric diphosphine ligands,Macromolecular Chemistry and Physics,ドイツ,Wiley-VCH,1996年 1月,vol.197, No.1,p.355-365
Wolfgang A. Herrmann, Christoph Brossmer, Claus-Peter Reisinger, Thomas H. Riermeier, Karl Ofere, Matthias Beller,Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides,Chemistry - A European Journal,ドイツ,Wiley-VCH,1997年 8月,vol.3, No.8,p.1357-1364
D. F. Gill, B. E. Mann, B. L. Shaw,Transition Metal-Carbon Bonds. Part XXXIII. International Metallations of Secondary and Tertiary Carbon Atoms by Platinum(II) and Palladium(II),Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1973年 3月,No.3,p.270-278
H. David Empsall, Peter N. heys, Bernard L. Shaw,Complexes of Platinum and Palladium with Tertiary Dimethoxyphenylphosphines: Attempts to Effect O- or C-Metallation,Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1978年 3月,No.3,p.257-262
Christopher E. Jones, Bernard L. Shaw, Brian L. Turtle,O- and C-Metallation of 2-Alkoxyphenylphosphines by Platinum(II),Journal of the Chemical Society, Dalton Transactions,英国,Royal Society of Chemistry,1974年 6月,No.9,p.992-999
Thomas Langer, Jorg Janssen, Gunter Helmchen,Catalytic Asymmetric Hydrosilylation of Ketones Using Rhodium-(I)-Complexes of Chiral Phosphinooxazoline Ligands,Tetrahedron Asymmetry,NL,Elsevier Science,1996年 6月 1日,vol.7, No.6,p.1599-1602
Toshihide Yamamoto, Masakazu Nishiyama, Yasuyuki Koie,Palladium-Catalyzed Synthesis of Triarylamines from Aryl Halides and Diarylamines,Tetrahedron Letters,NL,Elsevier Science,1998年 4月16日,vol.39, No.7,p.2367-2370
Masakazu Nishiyama, Toshihide Yamamoto, Yasuyuki Koie,Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine inder a Palladium Tri-tert-butylphosphine Catalyst,Tetrahedron Letters,NL,Elsevier Science,1998年 2月12日,vol.39, No.7,p.617-620
Nagavelli Prabhakae Reddy, Masato Tanaka,Palladium-Catalyzed Amination of Aryl Chlorides,Tetrahedron Letters,NL,Elsevier Science,1997年 7月 7日,vol.38, No.27,p.4807-4810
Attila Aranyos, David W. Old, Ayumu Kiyomori, John P. Wolfe, Joseph P. Sadighi, Stephen L. Buchwald,Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers,Journal of the American Chemical Society,米国,ACS Publications,1999年 5月12日,vol.121, No.18,p.4369-4378
Stepan Vyskocil, Martin Smrcina, Vladimir Hanus, Miroslav Polasek, Pavel Kocovsky,Derivatives of 2-Amino-2'-diphenylphosphino-1,1'-binaphthyl (MAP) and Their Application in Asymmetric Palladium(0)-Catalyzed Allylic Substitution,Journal of Organic Chemistry,英国,Royal Society of Chemistry,1998年10月30日,Vol.63, No.22,p.7738-7748
Kuiling Ding, Yang Wang, Hongying Yun, Jinxia Liu, Yangjie Wu, Masahiro Terada, Yasutaka Okubo, Koichi Mikami,Highly Effect and Practical Optical Resolution of 2-Amino-2'-hydroxy-1,1'-binaphthyl by Molecular Complexation with N-Benzylcinchonidium Chloride: A Direct Transformation to Binaphthyl Amino Phosphine,Chemistry - A European Journal,ドイツ,Wiley-VCH,1999年 6月 4日,vol.5, No.6,p.1734-1737
David W. Old, John P. Wolfe, Stephen L. Buchwald,A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Tmperature Suzuki Couplings and Amination of Unactivated Aryl CHlorides,Journal of the American Chemical Society,米国,ACS Publications,1998年 9月23日,vol.120, No.37,p.9722-9723
Blake C. Hamann, John F. Hartwig,Sterically Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and CHlorides, and the First Amination of Aryl Tosylates,Journal of the American Chemical Society,米国,ACS Publications,1998年 7月29日,vol.120, No.29,p.7369-7370
John P. Wolfe, Robert A. Singer, Bryant H. Yang, Stephen L. Buchwald,Highly Active Palladium Catalysts for Suzuki Coupling Reactions,Journal of the American Chemical Society,米国,ACS Publications,1999年10月20日,vol.121, No.41,p.9550-9561
John P. Wolfe, Stephen L. Buchwald,A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides,Angewandte Chemie International Edition,ドイツ,Wiley-VCH,1999年 8月12日,vol.38, No.16,p.2413-2416
Attorney, Agent or Firm:
Yanagita Seiji
Go Sakuma
Go Sakuma