Title:
CATALYST FOR HYDROSILYLATION REACTION, HYDROGENATION REACTION, AND HYDROSILANE REDUCTION REACTION
Document Type and Number:
WIPO Patent Application WO/2018/159595
Kind Code:
A1
Abstract:
Provided is a catalyst which comprises a compound represented by formula (1) and which exhibits activity for at least one type of reaction selected from among hydrosilylation reaction or hydrogenation reaction with respect to an aliphatic unsaturated bond and hydrosilane reduction reaction with respect to a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond. Formula (1): Mn(Lm) {M represents Fe, Co, or Ni having an oxidation number of 0, L represents an isocyanide ligand represented by formula (2), n denotes an integer of 1-8, and m denotes an integer of 2-12. Formula (2): (CN)x-R1 (R1 represents a mono- to trivalent-organic group having 1-30 carbon atoms, optionally being substituted by a halogen atom, and optionally having interposed therein one or more atoms selected from among O, N, S, and Si; and x denotes an integer of 1-3.)}.
Inventors:
NAGASHIMA HIDEO (JP)
SANAGAWA ATSUSHI (JP)
KAWABATA SHOMA (JP)
NODA DAISUKE (JP)
SAKUTA KOJI (JP)
SANAGAWA ATSUSHI (JP)
KAWABATA SHOMA (JP)
NODA DAISUKE (JP)
SAKUTA KOJI (JP)
Application Number:
PCT/JP2018/007204
Publication Date:
September 07, 2018
Filing Date:
February 27, 2018
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
SHINETSU CHEMICAL CO (JP)
SHINETSU CHEMICAL CO (JP)
International Classes:
B01J31/22; C07C5/03; C07C9/15; C07C15/073; C07C209/50; C07C211/27; C07F7/08; C07F7/10; C08G77/08; C07B61/00
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| WO2016024607A1 | 2016-02-18 | |||
| WO2016027819A1 | 2016-02-25 | |||
| WO2013081794A1 | 2013-06-06 | |||
| WO2010016416A1 | 2010-02-11 | |||
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G. K. BARKER ET AL.: "Synthesis and Reactions of Octakis (t- butyl isocyanide) dicobal t and Pentakis (t-buty 1 isocyanide) ruthenium; X-Ray Crystal and Molecular Structures of [Co2 (ButNC) 8] and[Ru(Ph3P) (ButNC) 4] '', Journal of the Chemical Society", CHEMICAL COMMUNICATIONS, vol. 8, 1977, pages 256 - 258, XP055539842
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P. J. CHIRIK ET AL., J. AM. CHEM. SOC., vol. 126, 2004, pages 13794
P. J. CHIRIK ET AL., SCIENCE, vol. 335, 2012, pages 567
J. CHEN ET AL., ANGEW. CHEM. INT. ED., vol. 54, 2015, pages 4661
A. J. CHALK ET AL., J. AM. CHEM. SOC., vol. 87, 1965, pages 1133
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A. J. CHALK ET AL., J. ORGANOMET. CHEM., vol. 21, 1970, pages 207
N. SONODA ET AL., J. ORG. CHEM., vol. 52, 1987, pages 4864
S. MURAI ET AL., CHEM. LETT., 2000, pages 14
E. L.MUETTERTIES ET AL., INORG. CHEM., vol. 19, 1980, pages 1552
B. E. GRANT ET AL., J. AM. CHEM. SOC., vol. 115, 1993, pages 2151
L. DENG ET AL., ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 10845
P. HOLLAD ET AL., J. AM. CHEM. SOC., vol. 137, 2015, pages 13244
P. J. CHIRIK ET AL., ACS CATAL., vol. 6, 2016, pages 2632
H. NAGASHIMA ET AL., ORGANOMETALLICS, vol. 34, 2015, pages 2896
P. J. CHIRIK ET AL., J. AM. CHEM. SOC., vol. 138, 2016, pages 11907
L. V. VRANKEN ET AL., J. ORG. CHEM., vol. 66, 2001, pages 7270
S. V. KIRPICHENKO ET AL., J. ORGANOMET. CHEM., vol. 190, 1980, pages 335
KATO ET AL., ORGANOMETALLICS, vol. 17, 1998, pages 926
M. UMENO ET AL., J. ORGANOMET. CHEM., vol. 50, 1973, pages 297
I. KOWNACKI ET AL., J. ORGANOMET. CHEM., vol. 597, 2000, pages 175
P. VALERGA ET AL., DALTON TRANS., 2007, pages 3000
T. D. TILLEY ET AL., CHEM. COMMUN., vol. 48, 2012, pages 7146
E, N, FRANKEL ET AL., J. ORG. CHEM., vol. 29, 1964, pages 3292
M. S. WRIGHTON ET AL., J. AM. CHEM. SOC., vol. 98, 1976, pages 551
R. E. HARMON ET AL., J. CHEM, REV., vol. 73, 1973, pages 21
J. G. DE VRIES ET AL., DALTON TRANS., vol. 39, 2010, pages 8464
A. J. WANGELIN ET AL., GREEN CHEM., vol. 17, 2015, pages 1408
J. C. PETERS ET AL., INORG. CHEM., vol. 43, 2004, pages 7474
H. NAGASHIMA ET AL., CHEM. COMMUN., vol. 47, 2011, pages 6581
P. J. CHIRIK ET AL., ACS CATAL., vol. 2, 2012, pages 1760
J. C. PETERS ET AL., J. AM. CHEM. SOC., vol. 135, 2013, pages 15310
W. R. BROWN, ORGANIC REACTIONS, vol. 6, 1941, pages 470
H. NAGASHIMA ET AL., ANGEW. CHEM. INT. ED., vol. 48, 2009, pages 9511
M. BELLER ET AL., ANGEW. CHEM. INT.ED., vol. 48, 2009, pages 9507
H. NISHIYAMA ET AL., ANGEW. CHEM. INT. ED., vol. 49, 2010, pages 9384
H. NISHIYAMA ET AL., CHEM. EUR. J., vol. 16, 2010, pages 3090
M. BELLER ET AL., ANGEW. CHEM., vol. 51, 2012, pages 1662
SORTAIS ET AL., ADV. SYNTH. CATAL., vol. 355, 2013, pages 3358
Z. LU ET AL., CHEM. COMMUN., 2015, pages 5725
T. MURAI ET AL., J. ORG. CHEM., vol. 55, 1990, pages 449
F. G. A. STONE ET AL., J. CHEM. SOC., DALTON TRANS., 1979, pages 1003
W. C. WOLSEY ET AL., J. CHEM. SOC., DALTON TRANS., 1981, pages 219
N. J. COVILLE ET AL., J. CHEM. SOC., DALTON TRANS., 1982, pages 1069
W. D. JONES ET AL., INORG. CHEM., vol. 26, 1987, pages 2120
D. LENTZ, J. ORGANOMET. CHEM., vol. 377, 1989, pages 305
J. S. FIGUEROA ET AL., INORG. CHEM., vol. 54, 2015, pages 5579
Y. YAMAMOTO ET AL., INORG. CHEM., vol. 17, 1978, pages 3111
P. WOODWARD ET AL., J. CHEM. SOC., DALTON TRANS., 1980, pages 80
N. J. COOPER ET AL., J. AM. CHEM. SOC., vol. 116, 1994, pages 8566
J. S. FIGUEROA ET AL., J. AM. CHEM. SOC., vol. 132, 2010, pages 5033
E. L.MUETTERTIES ET AL., J. AM. CHEM. SOC., vol. 99, 1977, pages 743
D. LENTZ ET AL., J. FLUORINE CHEM., vol. 89, 1998, pages 73
ORGANOMETALLICS, vol. 23, 2004, pages 3976 - 3981
ORG. SYNTH., vol. 90, 2013, pages 358 - 366
TETRAHEDRON LETTERS, vol. 17, 1972, pages 1637 - 1640
CHEM. REV., vol. 96, 1996, pages 887 - 910
See also references of EP 3590596A4
W. D. JONES ET AL.: "Preparation and Structural Examination of a Series of New, Low-Valent Iron Phosphine Isocyanide Complexes with Bent C-N-C Linkages", INORG. CHEM., vol. 26, no. 13, 1987, pages 2120 - 2127, XP055539823
G. K. BARKER ET AL.: "Synthesis and Reactions of Octakis (t- butyl isocyanide) dicobal t and Pentakis (t-buty 1 isocyanide) ruthenium; X-Ray Crystal and Molecular Structures of [Co2 (ButNC) 8] and[Ru(Ph3P) (ButNC) 4] '', Journal of the Chemical Society", CHEMICAL COMMUNICATIONS, vol. 8, 1977, pages 256 - 258, XP055539842
A. N. NESMEYANOV ET AL., TETRAHEDRON, vol. 17, 1962, pages 61
M. S. WRIGHTON ET AL., J. ORGANOMET. CHEM., vol. 128, 1977, pages 345
F. KAKIUCHI ET AL., J. ORGANOMET. CHEM., vol. 456, 1993, pages 45
H. NAKAZAWA ET AL., J. AM. CHEM. SOC., vol. 134, 2012, pages 804
P. J. CHIRIK ET AL., ORGANOMETALLICS, vol. 31, 2012, pages 2175
P. J. CHIRIK ET AL., J. AM. CHEM. SOC., vol. 126, 2004, pages 13794
P. J. CHIRIK ET AL., SCIENCE, vol. 335, 2012, pages 567
J. CHEN ET AL., ANGEW. CHEM. INT. ED., vol. 54, 2015, pages 4661
A. J. CHALK ET AL., J. AM. CHEM. SOC., vol. 87, 1965, pages 1133
A. J. CHALK ET AL., J. AM. CHEM. SOC., vol. 89, 1967, pages 1640
A. J. CHALK ET AL., J. ORGANOMET. CHEM., vol. 21, 1970, pages 207
N. SONODA ET AL., J. ORG. CHEM., vol. 52, 1987, pages 4864
S. MURAI ET AL., CHEM. LETT., 2000, pages 14
E. L.MUETTERTIES ET AL., INORG. CHEM., vol. 19, 1980, pages 1552
B. E. GRANT ET AL., J. AM. CHEM. SOC., vol. 115, 1993, pages 2151
L. DENG ET AL., ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 10845
P. HOLLAD ET AL., J. AM. CHEM. SOC., vol. 137, 2015, pages 13244
P. J. CHIRIK ET AL., ACS CATAL., vol. 6, 2016, pages 2632
H. NAGASHIMA ET AL., ORGANOMETALLICS, vol. 34, 2015, pages 2896
P. J. CHIRIK ET AL., J. AM. CHEM. SOC., vol. 138, 2016, pages 11907
L. V. VRANKEN ET AL., J. ORG. CHEM., vol. 66, 2001, pages 7270
S. V. KIRPICHENKO ET AL., J. ORGANOMET. CHEM., vol. 190, 1980, pages 335
KATO ET AL., ORGANOMETALLICS, vol. 17, 1998, pages 926
M. UMENO ET AL., J. ORGANOMET. CHEM., vol. 50, 1973, pages 297
I. KOWNACKI ET AL., J. ORGANOMET. CHEM., vol. 597, 2000, pages 175
P. VALERGA ET AL., DALTON TRANS., 2007, pages 3000
T. D. TILLEY ET AL., CHEM. COMMUN., vol. 48, 2012, pages 7146
E, N, FRANKEL ET AL., J. ORG. CHEM., vol. 29, 1964, pages 3292
M. S. WRIGHTON ET AL., J. AM. CHEM. SOC., vol. 98, 1976, pages 551
R. E. HARMON ET AL., J. CHEM, REV., vol. 73, 1973, pages 21
J. G. DE VRIES ET AL., DALTON TRANS., vol. 39, 2010, pages 8464
A. J. WANGELIN ET AL., GREEN CHEM., vol. 17, 2015, pages 1408
J. C. PETERS ET AL., INORG. CHEM., vol. 43, 2004, pages 7474
H. NAGASHIMA ET AL., CHEM. COMMUN., vol. 47, 2011, pages 6581
P. J. CHIRIK ET AL., ACS CATAL., vol. 2, 2012, pages 1760
J. C. PETERS ET AL., J. AM. CHEM. SOC., vol. 135, 2013, pages 15310
W. R. BROWN, ORGANIC REACTIONS, vol. 6, 1941, pages 470
H. NAGASHIMA ET AL., ANGEW. CHEM. INT. ED., vol. 48, 2009, pages 9511
M. BELLER ET AL., ANGEW. CHEM. INT.ED., vol. 48, 2009, pages 9507
H. NISHIYAMA ET AL., ANGEW. CHEM. INT. ED., vol. 49, 2010, pages 9384
H. NISHIYAMA ET AL., CHEM. EUR. J., vol. 16, 2010, pages 3090
M. BELLER ET AL., ANGEW. CHEM., vol. 51, 2012, pages 1662
SORTAIS ET AL., ADV. SYNTH. CATAL., vol. 355, 2013, pages 3358
Z. LU ET AL., CHEM. COMMUN., 2015, pages 5725
T. MURAI ET AL., J. ORG. CHEM., vol. 55, 1990, pages 449
F. G. A. STONE ET AL., J. CHEM. SOC., DALTON TRANS., 1979, pages 1003
W. C. WOLSEY ET AL., J. CHEM. SOC., DALTON TRANS., 1981, pages 219
N. J. COVILLE ET AL., J. CHEM. SOC., DALTON TRANS., 1982, pages 1069
W. D. JONES ET AL., INORG. CHEM., vol. 26, 1987, pages 2120
D. LENTZ, J. ORGANOMET. CHEM., vol. 377, 1989, pages 305
J. S. FIGUEROA ET AL., INORG. CHEM., vol. 54, 2015, pages 5579
Y. YAMAMOTO ET AL., INORG. CHEM., vol. 17, 1978, pages 3111
P. WOODWARD ET AL., J. CHEM. SOC., DALTON TRANS., 1980, pages 80
N. J. COOPER ET AL., J. AM. CHEM. SOC., vol. 116, 1994, pages 8566
J. S. FIGUEROA ET AL., J. AM. CHEM. SOC., vol. 132, 2010, pages 5033
E. L.MUETTERTIES ET AL., J. AM. CHEM. SOC., vol. 99, 1977, pages 743
D. LENTZ ET AL., J. FLUORINE CHEM., vol. 89, 1998, pages 73
ORGANOMETALLICS, vol. 23, 2004, pages 3976 - 3981
ORG. SYNTH., vol. 90, 2013, pages 358 - 366
TETRAHEDRON LETTERS, vol. 17, 1972, pages 1637 - 1640
CHEM. REV., vol. 96, 1996, pages 887 - 910
See also references of EP 3590596A4
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PATENT PROFESSIONAL CORPORATION EI-MEI PATENT OFFICE (JP)
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