Title:
METHOD FOR PRODUCING ALDEHYDE COMPOUND OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/166702
Kind Code:
A1
Abstract:
The present invention provides a method for accomplishing a reverse-Markovnikov type Wacker oxidation reaction using a terminal alkene that has a substituent in the β-position as a starting material. The present invention specifically provides a method for producing an aldehyde compound or a derivative thereof by reacting an alkene compound represented by general formula (1) in an aqueous solvent at least in the presence of a catalyst, wherein the aqueous solvent contains 60% by volume or more of at least one substance selected from the group consisting of water and acetone in the whole solvent. (In general formula (1), each of R1 and R2 independently represents a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alicyclic hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group; and R1 and R2 may combine with each other to form a ring.)
Inventors:
SHIMIZU YUHEI (JP)
URA YASUYUKI (JP)
URA YASUYUKI (JP)
Application Number:
PCT/JP2021/004462
Publication Date:
August 26, 2021
Filing Date:
February 05, 2021
Export Citation:
Assignee:
KURARAY CO (JP)
International Classes:
C07D307/20; C07B61/00
Domestic Patent References:
| WO2016144228A1 | 2016-09-15 |
Other References:
VORONOVA KRISZTINA, PURGEL MIHÁLY, UDVARDY ANTAL, BÉNYEI ATTILA C., KATHÓ ÁGNES, JOÓ FERENC: "Hydrogenation and Redox Isomerization of Allylic Alcohols Catalyzed by a New Water-Soluble Pd–tetrahydrosalen Complex", ORGANOMETALLICS, vol. 32, no. 15, 12 August 2013 (2013-08-12), pages 4391 - 4401, XP055849424, ISSN: 0276-7333, DOI: 10.1021/om400555u
PARK YONGHO, KOGA YUMI, SU CINDY, WATERBURY AMANDA L., JOHNNY CHRISTOPHER L., LIAU BRIAN B.: "Versatile Synthetic Route to Cycloheximide and Analogues That Potently Inhibit Translation Elongation", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 58, no. 16, 8 April 2019 (2019-04-08), DE, pages 5387 - 5391, XP055849760, ISSN: 1433-7851, DOI: 10.1002/anie.201901386
TONG JINHUI; CAI XIAODONG; WANG HAIYAN; XIA CHUNGU: "Efficient magnetic CoFe2O4 nanocrystal catalyst for aerobic oxidation of cyclohexane prepared by sol–gel auto-combustion method: effects of catalyst preparation parameters", JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY, vol. 66, no. 3, 9 April 2013 (2013-04-09), US, pages 452 - 459, XP035374207, ISSN: 0928-0707, DOI: 10.1007/s10971-013-3031-8
KAZUHIRO SUGIOKA, MASAHARU UCHIYAMA, TAKEHIKO SUZUKI, YASUO YAMAZAKI: "Reaction of Diaryliodonium Salts with Olefins Catalyzed by Palladium Compoundst", JOURNAL OF THE CHEMICAL SOCIETY OF JAPAN, vol. 1985, no. 3, 10 March 1985 (1985-03-10), JP, pages 527 - 532, XP055849775, ISSN: 0369-4577, DOI: 10.1246/nikkashi.1985.527
SAIMOTO H.; ET AL: "Synthesis of 3,4-Dihydro-2H-Benzopyrans from phenols and alpha,beta-unsaturated carbonyl compound.", HETEROCYCLES, vol. 55, no. 11, 1 January 2001 (2001-01-01), JP, pages 2051 - 2054, XP008084494, ISSN: 0385-5414, DOI: 10.3987/COM-01-9333
TAKAHASHI KAZUNORI, WATANABE MASAYUKI, HONDA TOSHIO: "Highly Efficient Stereocontrolled Total Synthesis of (+)-Upial", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 47, no. 1, 1 January 2008 (2008-01-01), DE, pages 131 - 133, XP055849795, ISSN: 1433-7851, DOI: 10.1002/anie.200704423
ODDON FRÉDÉRIC, GIRGENTI ELODIE, LEBRUN COLETTE, MARCHI-DELAPIERRE CAROLINE, PÉCAUT JACQUES, MÉNAGE STÉPHANE: "Iron Coordination Chemistry of N2Py2 Ligands Substituted by Carboxylic Moieties and Their Impact on Alkene Oxidation Catalysis", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 2012, no. 1, 1 January 2012 (2012-01-01), DE, pages 85 - 96, XP055849801, ISSN: 1434-1948, DOI: 10.1002/ejic.201100785
HO, T.-L., CHANG, M.H., CHEN, C.: "Abnormal and regioselective Wacker oxidation of 1,5-dienes", TETRAHEDRON LETTERS, vol. 44, no. 36, 1 September 2003 (2003-09-01), pages 6955 - 6957, XP004444442, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(03)01709-X
PARK YONGHO, KOGA YUMI, SU CINDY, WATERBURY AMANDA L., JOHNNY CHRISTOPHER L., LIAU BRIAN B.: "Versatile Synthetic Route to Cycloheximide and Analogues That Potently Inhibit Translation Elongation", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 58, no. 16, 8 April 2019 (2019-04-08), DE, pages 5387 - 5391, XP055849760, ISSN: 1433-7851, DOI: 10.1002/anie.201901386
TONG JINHUI; CAI XIAODONG; WANG HAIYAN; XIA CHUNGU: "Efficient magnetic CoFe2O4 nanocrystal catalyst for aerobic oxidation of cyclohexane prepared by sol–gel auto-combustion method: effects of catalyst preparation parameters", JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY, vol. 66, no. 3, 9 April 2013 (2013-04-09), US, pages 452 - 459, XP035374207, ISSN: 0928-0707, DOI: 10.1007/s10971-013-3031-8
KAZUHIRO SUGIOKA, MASAHARU UCHIYAMA, TAKEHIKO SUZUKI, YASUO YAMAZAKI: "Reaction of Diaryliodonium Salts with Olefins Catalyzed by Palladium Compoundst", JOURNAL OF THE CHEMICAL SOCIETY OF JAPAN, vol. 1985, no. 3, 10 March 1985 (1985-03-10), JP, pages 527 - 532, XP055849775, ISSN: 0369-4577, DOI: 10.1246/nikkashi.1985.527
SAIMOTO H.; ET AL: "Synthesis of 3,4-Dihydro-2H-Benzopyrans from phenols and alpha,beta-unsaturated carbonyl compound.", HETEROCYCLES, vol. 55, no. 11, 1 January 2001 (2001-01-01), JP, pages 2051 - 2054, XP008084494, ISSN: 0385-5414, DOI: 10.3987/COM-01-9333
TAKAHASHI KAZUNORI, WATANABE MASAYUKI, HONDA TOSHIO: "Highly Efficient Stereocontrolled Total Synthesis of (+)-Upial", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 47, no. 1, 1 January 2008 (2008-01-01), DE, pages 131 - 133, XP055849795, ISSN: 1433-7851, DOI: 10.1002/anie.200704423
ODDON FRÉDÉRIC, GIRGENTI ELODIE, LEBRUN COLETTE, MARCHI-DELAPIERRE CAROLINE, PÉCAUT JACQUES, MÉNAGE STÉPHANE: "Iron Coordination Chemistry of N2Py2 Ligands Substituted by Carboxylic Moieties and Their Impact on Alkene Oxidation Catalysis", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 2012, no. 1, 1 January 2012 (2012-01-01), DE, pages 85 - 96, XP055849801, ISSN: 1434-1948, DOI: 10.1002/ejic.201100785
HO, T.-L., CHANG, M.H., CHEN, C.: "Abnormal and regioselective Wacker oxidation of 1,5-dienes", TETRAHEDRON LETTERS, vol. 44, no. 36, 1 September 2003 (2003-09-01), pages 6955 - 6957, XP004444442, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(03)01709-X
Attorney, Agent or Firm:
OHTANI PATENT OFFICE (JP)
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