WO2007007084A3 - Copper (ii) catalysed additions to alkenes - Google Patents

Copper (ii) catalysed additions to alkenes Download PDF

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Publication number
WO2007007084A3
WO2007007084A3 PCT/GB2006/002558 GB2006002558W WO2007007084A3 WO 2007007084 A3 WO2007007084 A3 WO 2007007084A3 GB 2006002558 W GB2006002558 W GB 2006002558W WO 2007007084 A3 WO2007007084 A3 WO 2007007084A3
Authority
WO
WIPO (PCT)
Prior art keywords
copper
catalysed
alkenes
additions
nucleophile
Prior art date
Application number
PCT/GB2006/002558
Other languages
French (fr)
Other versions
WO2007007084A2 (en
Inventor
King Kuok Mimi Hii
Original Assignee
Ic Innovations Ltd
King Kuok Mimi Hii
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
Priority claimed from GB0514321A external-priority patent/GB0514321D0/en
Priority claimed from GB0609666A external-priority patent/GB0609666D0/en
Application filed by Ic Innovations Ltd, King Kuok Mimi Hii filed Critical Ic Innovations Ltd
Publication of WO2007007084A2 publication Critical patent/WO2007007084A2/en
Publication of WO2007007084A3 publication Critical patent/WO2007007084A3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/05Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/04Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D315/00Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/36Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

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

Abstract

The present invention relates to a process for the addition of a nucleophile to a substrate comprising an alkene, in the presence of a copper (II) catalyst, wherein the nucleophile is preferably a compound having the formula R1-XH wherein X is NR6, O, C(O)O, OCONH2, SO2NH2, CONH2, S, P or Si.
PCT/GB2006/002558 2005-07-12 2006-07-10 Copper (ii) catalysed additions to alkenes WO2007007084A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0514321A GB0514321D0 (en) 2005-07-12 2005-07-12 Synthesis
GB0514321.9 2005-07-12
GB0609666.3 2006-05-15
GB0609666A GB0609666D0 (en) 2006-05-15 2006-05-15 Synthesis

Publications (2)

Publication Number Publication Date
WO2007007084A2 WO2007007084A2 (en) 2007-01-18
WO2007007084A3 true WO2007007084A3 (en) 2007-03-01

Family

ID=37560709

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2006/002558 WO2007007084A2 (en) 2005-07-12 2006-07-10 Copper (ii) catalysed additions to alkenes

Country Status (1)

Country Link
WO (1) WO2007007084A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2950050A1 (en) * 2009-09-14 2011-03-18 Cray Valley Sa PROCESS FOR THE PREPARATION OF CYCLOALIPHATIC METHACRYLIC ESTERS BY CATALYSIS BASED ON TRIFLIC ACID AND DERIVATIVES THEREOF
WO2012047686A1 (en) 2010-10-05 2012-04-12 Trustees Of Dartmouth College Hydrothiolation of unactivated alkenes
CN103237824B (en) 2010-12-21 2015-07-22 3M创新有限公司 Polymers derived from secondary alkyl (meth)acrylates

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4204997A (en) * 1979-03-19 1980-05-27 Monsanto Company Asymmetric amination of 1,3-dienes
US20020016509A1 (en) * 2000-03-01 2002-02-07 Yale University Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4204997A (en) * 1979-03-19 1980-05-27 Monsanto Company Asymmetric amination of 1,3-dienes
US20020016509A1 (en) * 2000-03-01 2002-02-07 Yale University Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BARLUENGA J ET AL: "AN EFFICIENT METHOD FOR THE COPPER(II)-PROMOTED STEREOSELECTIVE IODOFUNCTIONALIZATION OF ALKENES", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY. LETCHWORTH, GB, 1990, pages 2807 - 2809, XP009044918, ISSN: 0300-922X *
DORTA ET AL: "The [IrCl(Diphosphine)]2/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 119, no. 44, 5 November 1997 (1997-11-05), pages 10857 - 10858, XP002110586, ISSN: 0002-7863 *
KRAUSE ET AL: "Recent Advances in Catalytic Enantioselective Michael Additions", SYNTHESIS, vol. 2, 2001, pages 171 - 196, XP009076685 *
LI KELIN ET AL: "Asymmetric synthesis of .beta.-amino acid and amide derivatives by catalytic conjugate addition of aromatic amines to N-alkenoylcarbamates", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH VERLAG, WEINHEIM, DE, no. 5, 2004, pages 959 - 964, XP002382490, ISSN: 1434-193X *
UTSUNOMIYA MASARU ET AL: "Intermolecular, Markovnikov hydroamination of vinylarenes with alkylamines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 125, no. 47, 2003, pages 14286 - 14287, XP002382489, ISSN: 0002-7863 *

Also Published As

Publication number Publication date
WO2007007084A2 (en) 2007-01-18

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