JP5788392B2 - 高度にｚ−選択的なオレフィンメタセシス - Google Patents

高度にｚ−選択的なオレフィンメタセシス Download PDF

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JP5788392B2
JP5788392B2 JP2012532065A JP2012532065A JP5788392B2 JP 5788392 B2 JP5788392 B2 JP 5788392B2 JP 2012532065 A JP2012532065 A JP 2012532065A JP 2012532065 A JP2012532065 A JP 2012532065A JP 5788392 B2 JP5788392 B2 JP 5788392B2
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pyr
nar
chcme
ligand
reaction
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JP2013506663A (ja
JP2013506663A5 (https=
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リチャード アール． シュロック，
リチャード アール． シュロック，
アニー ジェイ． キング，
アニー ジェイ． キング，
ユー シャオ，
ユー シャオ，
マーガレット エム． フルック，
マーガレット エム． フルック，
アミール エイチ． ホベイダ，
アミール エイチ． ホベイダ，
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Massachusetts Institute of Technology
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Massachusetts Institute of Technology
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    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
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    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
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    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2012532065A 2009-09-30 2010-09-30 高度にｚ−選択的なオレフィンメタセシス Expired - Fee Related JP5788392B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12/571,036 2009-09-30
US12/571,036 US8362311B2 (en) 2009-09-30 2009-09-30 Highly Z-selective olefins metathesis
PCT/US2010/002644 WO2011040963A1 (en) 2009-09-30 2010-09-30 Highly z-selective olefin metathesis

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JP2013506663A JP2013506663A (ja) 2013-02-28
JP2013506663A5 JP2013506663A5 (https=) 2014-07-17
JP5788392B2 true JP5788392B2 (ja) 2015-09-30

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US (4) US8362311B2 (https=)
EP (1) EP2483224A1 (https=)
JP (2) JP5788392B2 (https=)
CN (2) CN102781888B (https=)
CA (1) CA2776035A1 (https=)
WO (1) WO2011040963A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015214571A (ja) * 2009-09-30 2015-12-03 マサチューセッツ インスティテュート オブ テクノロジー 高度にｚ−選択的なオレフィンメタセシス

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7932397B2 (en) 2006-11-22 2011-04-26 Massachusetts Institute Of Technology Olefin metathesis catalysts and related methods
US8222469B2 (en) * 2009-07-15 2012-07-17 Massachusetts Institute Of Technology Catalysts and processes for the formation of terminal olefins by ethenolysis
EP2556078B1 (de) 2010-04-03 2014-09-24 Studiengesellschaft Kohle MbH Katalysatoren für die alkinmetathese
GB2486631A (en) * 2010-12-01 2012-06-27 Univ Sheffield Phenol/quinone boronic acids/esters and method of preparation thereof
DE102011012629A1 (de) 2011-02-28 2012-08-30 Studiengesellschaft Kohle Mbh Metallkomplexe des Molybdäns und Wolframs und ihre Verwendung als Präkatalysatoren für die Olefinmetathese
US8546500B2 (en) 2011-05-27 2013-10-01 Massachusetts Institute Of Technology Complexes for use in metathesis reactions
CN103797009B (zh) 2011-06-03 2017-04-26 麻省理工学院 Z‑选择性闭环复分解反应
WO2012171652A1 (en) 2011-06-17 2012-12-20 Ximo Ag Synthesis of vitamin e
ES2736603T3 (es) 2011-11-07 2020-01-03 Massachusetts Inst Technology Complejos de wolframio oxo alquilideno para la metátesis de olefinas selectiva de Z
JP2015506335A (ja) * 2011-12-20 2015-03-02 ディーエスエム アイピー アセッツ ビー．ブイ． ９−オクタデセン二酸からのアゼライン酸の製造方法
EP2703081B1 (en) 2012-09-04 2019-08-07 XiMo AG Molybdenum and tungsten complexes as olefin metathesis catalysts and reactions using the catalysts
CN105555402B (zh) * 2013-03-14 2019-03-22 西莫有限公司 复分解催化剂及使用该催化剂的反应
WO2014169014A1 (en) 2013-04-09 2014-10-16 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
WO2014172534A1 (en) 2013-04-17 2014-10-23 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US9441059B2 (en) 2013-06-20 2016-09-13 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US10071950B2 (en) 2013-07-12 2018-09-11 Ximo Ag Use of immobilized molybdenum- and tungsten-containing catalysts in olefin cross metathesis
US10427146B2 (en) 2013-10-01 2019-10-01 Ximo Ag Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis
GB201404468D0 (en) * 2014-03-13 2014-04-30 Givaudan Sa Process
GB201406591D0 (en) * 2014-04-11 2014-05-28 Ximo Ag Compounds
WO2016014954A1 (en) * 2014-07-25 2016-01-28 California Institute Of Technology Tandem z-selective metathesis / dihydroxylation
FR3039546B1 (fr) * 2015-07-31 2017-08-11 Ifp Energies Now Procede de metathese des olefines utilisant un catalyseur contenant du silicium et du molybdene
DE102015215997A1 (de) * 2015-08-21 2017-02-23 Evonik Degussa Gmbh Phenol-Aren-Kupplungsprodukt
CN105111228A (zh) * 2015-08-28 2015-12-02 南京大学 具有5,5′-联四氢萘酮骨架的手性磷酸及其制备方法
WO2017087710A2 (en) * 2015-11-18 2017-05-26 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
EP3376859B1 (en) 2015-11-18 2021-01-06 Provivi, Inc. Microorganisms for the production of insect pheromones and related compounds
EP3394074B1 (en) 2015-12-23 2019-10-09 XiMo AG Immobilized metal alkylidene catalysts and use thereof in olefin metathesis
WO2017214133A2 (en) 2016-06-06 2017-12-14 Provivi, Inc. Semi-biosynthetic production of fatty alcohols and fatty aldehydes
US10183899B2 (en) 2016-11-10 2019-01-22 Chevron Phillips Chemical Company Lp Normal alpha olefin synthesis using metathesis and dehydroformylation
HUE073559T2 (hu) 2017-02-17 2026-01-28 Provivi Inc Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül
MX382401B (es) 2017-05-17 2025-03-13 Provivi Inc Microorganismos para la producción de feromonas de insectos y compuestos relacionados.
WO2018220088A1 (en) 2017-05-30 2018-12-06 Ximo Ag Methods of making olefinic e- and z-isomers
US11123723B2 (en) 2018-02-26 2021-09-21 The Regents Of The University Of California Oxidative dehydroxymethylation of alcohols to produce olefins
EP3759063A1 (en) 2018-02-26 2021-01-06 Bischof, Steven M. Normal alpha olefin synthesis using dehydroformylation or dehydroxymethylation
EP3976565A1 (en) * 2019-05-27 2022-04-06 Verbio Vereinigte BioEnergie AG Tungsten imido alkylidene o-bitet and o-binol complexes and use thereof in olefin metathesis reactions
US10995049B2 (en) 2019-07-19 2021-05-04 California Institute Of Technology Total synthesis of prostaglandin J natural products and their intermediates
WO2021163533A1 (en) * 2020-02-14 2021-08-19 University Of Florida Research Foundation, Incorporated Cyclic polyacetylene and methods of preparing the same
US12151993B2 (en) 2021-09-10 2024-11-26 Chevron Phillips Chemical Company Lp Selective 1-hexene/1-octene production with 1-decene
WO2023217684A1 (en) 2022-05-10 2023-11-16 Signify Holding B.V. Regulation of fruit set in peppers by dynamically adapting the led lighting spectrum

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4727215A (en) * 1985-09-25 1988-02-23 Massachusetts Institute Of Technology Catalyst composition for effecting metathesis of olefins
US5055628A (en) 1990-09-11 1991-10-08 Ethyl Corporation Preparation of alpha-olefin by ethenolysis
JP3067031B2 (ja) * 1992-04-03 2000-07-17 カリフォルニア インスティチュート オブ テクノロジー オレフィンメタセシス重合方法
US5639900A (en) * 1993-12-29 1997-06-17 Metton America, Inc. Thermally activated olefin metathesis catalyst precursor
US5672802A (en) * 1996-03-19 1997-09-30 Shell Oil Company Process for the preparation of alpha olefins
US5889128A (en) 1997-04-11 1999-03-30 Massachusetts Institute Of Technology Living olefin polymerization processes
US6121473A (en) 1998-02-19 2000-09-19 Massachusetts Institute Of Technology Asymmetric ring-closing metathesis reactions
US6346652B1 (en) 1998-07-13 2002-02-12 Massachusetts Institute Of Technology Asymmetric ring-closing metathesis reactions involving achiral and meso substrates
US6215019B1 (en) * 1998-09-01 2001-04-10 Tilliechem, Inc. Synthesis of 5-decenyl acetate and other pheromone components
US6271325B1 (en) 1999-05-17 2001-08-07 Univation Technologies, Llc Method of polymerization
US6727396B2 (en) * 2001-01-25 2004-04-27 Abb Lummus Global, Inc. Process for the production of linear alpha olefins and ethylene
DE10206845A1 (de) * 2002-02-19 2003-08-28 Basf Ag Modifiziertes Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung
US6939982B2 (en) 2002-05-15 2005-09-06 The Trustees Of Boston College Recyclable chiral metathesis catalysts
US7220886B2 (en) 2004-10-27 2007-05-22 Catalytic Distillation Technologies Olefin metathesis
EP2094711B8 (de) * 2006-09-25 2018-03-28 Forschungsverbund Berlin e.V. Strukturmimetika prolinreicher peptide und ihre pharmazeutische verwendung
US7932397B2 (en) 2006-11-22 2011-04-26 Massachusetts Institute Of Technology Olefin metathesis catalysts and related methods
FR2917406B1 (fr) * 2007-06-13 2012-08-03 Arkema France Procede de synthese de diacides ou diesters a partir d'acides et/ou d'esters gras naturels
CN101205242A (zh) * 2007-09-30 2008-06-25 埃沃尼克德古萨有限责任公司 含有n-杂环卡宾配体的钌的亚烷基络合物及其在烯烃复分解反应中作为高活性高选择性催化剂的用途
BRPI0906685A2 (pt) 2008-01-25 2016-10-11 Massachusetts Inst Technology catalisadores para reações de metátese incluindo metátese de olefina enantiosseletiva, e métodos relacionados
DE102009027603A1 (de) 2009-07-10 2011-01-13 Robert Bosch Gmbh Verfahren zur Koordination von zumindest einem Antriebsaggregat
US8222469B2 (en) 2009-07-15 2012-07-17 Massachusetts Institute Of Technology Catalysts and processes for the formation of terminal olefins by ethenolysis
US8362311B2 (en) 2009-09-30 2013-01-29 Massachusetts Institute Of Technology Highly Z-selective olefins metathesis
EP2534140B1 (en) 2010-02-08 2018-04-11 Trustees of Boston College Efficient methods for z- or cis-selective cross-metathesis
US8546500B2 (en) 2011-05-27 2013-10-01 Massachusetts Institute Of Technology Complexes for use in metathesis reactions
CN103797009B (zh) 2011-06-03 2017-04-26 麻省理工学院 Z‑选择性闭环复分解反应
ES2736603T3 (es) 2011-11-07 2020-01-03 Massachusetts Inst Technology Complejos de wolframio oxo alquilideno para la metátesis de olefinas selectiva de Z
CN105555402B (zh) 2013-03-14 2019-03-22 西莫有限公司 复分解催化剂及使用该催化剂的反应
WO2014169014A1 (en) 2013-04-09 2014-10-16 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
WO2014172534A1 (en) 2013-04-17 2014-10-23 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US20140330018A1 (en) 2013-05-01 2014-11-06 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
US9441059B2 (en) 2013-06-20 2016-09-13 Massachusetts Institute Of Technology Metathesis catalysts and methods thereof
EP3019511B1 (en) 2013-07-12 2019-01-02 XiMo AG Immobilized metathesis tungsten catalysts and use thereof in olefin metathesis
EP3107655B1 (en) 2014-02-21 2024-05-08 Massachusetts Institute of Technology Catalysts and methods for ring opening metathesis polymerization

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015214571A (ja) * 2009-09-30 2015-12-03 マサチューセッツ インスティテュート オブ テクノロジー 高度にｚ−選択的なオレフィンメタセシス

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