WO2003006420A1 - Procede catalytique pour transformer des composes aryle en arylamines - Google Patents

Procede catalytique pour transformer des composes aryle en arylamines Download PDF

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Publication number
WO2003006420A1
WO2003006420A1 PCT/US2002/021919 US0221919W WO03006420A1 WO 2003006420 A1 WO2003006420 A1 WO 2003006420A1 US 0221919 W US0221919 W US 0221919W WO 03006420 A1 WO03006420 A1 WO 03006420A1
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WO
WIPO (PCT)
Prior art keywords
substituted
aryl
unsubstituted
group
compound
Prior art date
Application number
PCT/US2002/021919
Other languages
English (en)
Inventor
John F. Hartwig
Morten Jorgensen
Sunwoo Lee
Original Assignee
Yale University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yale University filed Critical Yale University
Publication of WO2003006420A1 publication Critical patent/WO2003006420A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/66—Preparation of compounds containing amino groups bound to a carbon skeleton from or via metallo-organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de transformation d'un composé aryle en un composé aniline, qui consiste à : (1) fournir un composé aryle contenant un groupe halure ou un groupe soufré; (2) faire réagir le composé aryle avec un réactif représenté par la structure (I), dans laquelle R1, R2, et R3 sont individuellement sélectionnés dans le groupe constitué par alkyle substitué ou non, alcényle substitué ou non, alcynyle substitué ou non, hétéroalkyle substitué ou non, aryle substitué ou non, hétéroaryle substitué ou non, arylalkyle substitué ou non, hétéroarylalkyle substitué ou non, ainsi que des combinaisons de ceux-ci; R4 est sélectionné dans le groupe constitué par hydrogène, alkyle substitué ou non, alcényle substitué ou non, alcynyle substitué ou non, hétéroalkyle substitué ou non, aryle substitué ou non, hétéroaryle substitué ou non, arylalkyle substitué ou non, hétéroarylalkyle substitué ou non, et SiR1R2R3; et A représente H ou un métal alcalin; l'opération de réaction est exécuté en présence d'un catalyseur de métal de transition du groupe 8 dans des conditions de réaction qui permettent d'obtenir un intermédiaire d'arylsilylamine, à condition que lorsque A représente H dans le réactif, l'opération de réaction comprend une base ; et enfin, (3) transformer l'intermédiaire d'arylsilylamine en composé aniline.
PCT/US2002/021919 2001-07-12 2002-07-11 Procede catalytique pour transformer des composes aryle en arylamines WO2003006420A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30485901P 2001-07-12 2001-07-12
US60/304,859 2001-07-12

Publications (1)

Publication Number Publication Date
WO2003006420A1 true WO2003006420A1 (fr) 2003-01-23

Family

ID=23178301

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/021919 WO2003006420A1 (fr) 2001-07-12 2002-07-11 Procede catalytique pour transformer des composes aryle en arylamines

Country Status (1)

Country Link
WO (1) WO2003006420A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1581467A2 (fr) * 2002-12-09 2005-10-05 Massachusetts Institute Of Technology Ligands pour métaux et processus a catalyse par métaux améliorés basés sur ces ligands
WO2006124283A1 (fr) * 2005-05-12 2006-11-23 Boehringer Ingelheim International, Gmbh Bis-amination d'halogenures d'aryle
WO2009050366A2 (fr) 2007-09-28 2009-04-23 Centre National De La Recherche Scientifique (C.N.R.S.) Procede de synthese d'arylamines
US7560596B2 (en) 2005-01-10 2009-07-14 Massachusetts Institute Of Technology Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
US7560582B2 (en) 1998-07-10 2009-07-14 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
US7586007B2 (en) 2007-04-03 2009-09-08 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US7759295B2 (en) 2007-04-03 2010-07-20 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US7858784B2 (en) 2007-12-12 2010-12-28 Massachusetts Institute Of Technology Ligands for transition-metal-catalyzed cross-couplings, and methods of use thereof
US7977286B2 (en) 2006-05-09 2011-07-12 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US8048833B2 (en) 2007-08-17 2011-11-01 Exxonmobil Research And Engineering Company Catalytic antioxidants
US8080601B2 (en) 2007-04-03 2011-12-20 Exxommobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
CN102993090A (zh) * 2012-10-11 2013-03-27 南通市华峰化工有限责任公司 一种2,6-二氨基吡啶的合成方法
JP2020091192A (ja) * 2018-12-05 2020-06-11 学校法人北里研究所 化合物及びその使用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HUANG ET AL.: "New ammonia equivalents for the Pd-catalyzed amination of aryl halides", ORG. LETT., vol. 3, no. 21, September 2001 (2001-09-01), pages 3417 - 3419, XP002958148 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7560582B2 (en) 1998-07-10 2009-07-14 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
EP1581467A4 (fr) * 2002-12-09 2008-08-13 Massachusetts Inst Technology Ligands pour métaux et processus a catalyse par métaux améliorés basés sur ces ligands
EP1581467A2 (fr) * 2002-12-09 2005-10-05 Massachusetts Institute Of Technology Ligands pour métaux et processus a catalyse par métaux améliorés basés sur ces ligands
US8735630B2 (en) 2005-01-10 2014-05-27 Massachusetts Institute Of Technology Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
US7560596B2 (en) 2005-01-10 2009-07-14 Massachusetts Institute Of Technology Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
US8378145B2 (en) 2005-01-10 2013-02-19 Massachusetts Institute Of Technology Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
WO2006124283A1 (fr) * 2005-05-12 2006-11-23 Boehringer Ingelheim International, Gmbh Bis-amination d'halogenures d'aryle
JP2008540526A (ja) * 2005-05-12 2008-11-20 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ハロゲン化アリールのビスアミノ化
US7977286B2 (en) 2006-05-09 2011-07-12 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US8080601B2 (en) 2007-04-03 2011-12-20 Exxommobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US7759295B2 (en) 2007-04-03 2010-07-20 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US7586007B2 (en) 2007-04-03 2009-09-08 Exxonmobil Research And Engineering Company Lubricating compositions containing ashless catalytic antioxidant additives
US8048833B2 (en) 2007-08-17 2011-11-01 Exxonmobil Research And Engineering Company Catalytic antioxidants
US8399680B2 (en) 2007-09-28 2013-03-19 Centre National De La Recherche Scientifique (C.N.R.S.) Arylamine synthesis method
WO2009050366A2 (fr) 2007-09-28 2009-04-23 Centre National De La Recherche Scientifique (C.N.R.S.) Procede de synthese d'arylamines
US7858784B2 (en) 2007-12-12 2010-12-28 Massachusetts Institute Of Technology Ligands for transition-metal-catalyzed cross-couplings, and methods of use thereof
CN102993090A (zh) * 2012-10-11 2013-03-27 南通市华峰化工有限责任公司 一种2,6-二氨基吡啶的合成方法
JP2020091192A (ja) * 2018-12-05 2020-06-11 学校法人北里研究所 化合物及びその使用
JP7193842B2 (ja) 2018-12-05 2022-12-21 学校法人北里研究所 化合物及びその使用

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