Did you know ? If you order before Friday 14h we deliver 90PCT of the the time next Tuesday, GENTAUR another in time delivery

Pubmed ID :28902495
Publication Date : 2017/09/13

Selective Synthesis of Primary Anilines from Cyclohexanone Oximes by the Concerted Catalysis of a Mg-Al Layered Double Hydroxide Supported Pd Catalyst.


Although the selective conversion of cyclohexanone oximes to primary anilines would be a good complement to the classical synthetic methods for primary anilines, which utilize arenes as the starting materials, there have been no general and efficient methods for the conversion of cyclohexanone oximes to primary anilines until now. In this study, we have successfully realized the efficient conversion of cyclohexanone oximes to primary anilines by utilizing a Mg-Al layered double hydroxide supported Pd catalyst (Pd(OH)x/LDH) under ligand-, additive-, and hydrogen-acceptor-free conditions. The substrate scope was very broad with respect to both cyclohexanone oximes and cyclohexenone oximes, which gave the corresponding primary anilines in high yields with high selectivities (17 examples, 75% to >99% yields). The reaction could be scaled up (gram-scale) with a reduced amount of the catalyst (0.2 mol %). Furthermore, the one-pot synthesis of primary anilines directly from cyclohexanones and hydroxylamine was also successful (five examples, 66-99% yields). The catalysis was intrinsically heterogeneous, and the catalyst could be reused for the conversion of cyclohexanone oxime to aniline at least five times with keeping its high catalytic performance. Kinetic studies and several control experiments showed that the high activity and selectivity of the present catalyst system were attributed to the concerted catalysis of the basic LDH support and the active Pd species on LDH. The present transformation of cyclohexanone oximes to primary anilines proceeds through a dehydration/dehydrogenation sequence, and herein the plausible reaction mechanism is proposed on the basis of several pieces of experimental evidence.

Authors : Jin Xiongjie , Koizumi Yu , Yamaguchi Kazuya , Nozaki Kyoko , Mizuno Noritaka ,

Related products :

Catalog number Product name Quantity
T-08854 TETRA EHTYL AMMONIUM BROMIDE 99 percent (Phase Transfer Catalyst) (For synthesis) CAS: 71-91-0 1 kg
T-08854 TETRA EHTYL AMMONIUM BROMIDE 99 percent (Phase Transfer Catalyst) (For synthesis) CAS: 71-91-0 250 gm
C-03135 CYCLOHEXANONE 99 percent (For Synthesis) CAS: 108-94-1 500 ml
C-03135 CYCLOHEXANONE 99 percent (For Synthesis) CAS: 108-94-1 2.5Ltr.
26-119 OXSM is a mitochondrial beta-ketoacyl synthase (EC 2.3.1.41) involved in mitochondrial fatty acid synthesis. It is required for catalysis of the chain-elongating condensation reaction.OXSM is a mitoch 0.05 mg
TM 612 LISTERIA SELECTIVE AGAR (DOUBLE PACK) (for selective isolation & cultivation of Listeria species from clinical samples) (Store below 8º C) 500 gm
TM 612 LISTERIA SELECTIVE AGAR (DOUBLE PACK) (for selective isolation & cultivation of Listeria species from clinical samples) (Store below 8º C) 500 gm
15932-80-6 Cyclohexanone, 5_methyl_2_(1 _methylet Cyclohexanone, 5_meth 1g
107389-91-3 Cyclohexanone,4_hydroxy_4_(2_hydroxye Cyclohexanone,4_hydro 1g
53608-84-7 Cyclohexanone diallylacetal Cyclohexanone diallyla 1g
TM 878 TEEPOL BROTH (DOUBLE PACK) (for selective isolation and identificat 500 gm
TM 878 TEEPOL BROTH (DOUBLE PACK) (for selective isolation and identificat 500 gm
TM 1454 MANNITOL SELENITE BROTH (DOUBLE PACK) (for selective enrichment of Salmonellae from clinical samples.) 500 gm
TM 1261 MODIFIED TEEPOL BROTH (DOUBLE PACK) (for selective isolation of enteric lactose fermenting ba 500 gm
TM 1261 MODIFIED TEEPOL BROTH (DOUBLE PACK) (for selective isolation of enteric lactose fermenting ba 500 gm
185036-38-8 Carulite catalyst Carulite catalyst 1g
30698-64-7 Cu_Tmeda Catalyst Cu_Tmeda Catalyst 1g
31-043 Cul1 may contribute to catalysis through the positioning of the substrate and the ubiquitin-conjugating enzyme 0.1 mg
TM 1223 LISTERIA ENRICHMENT BROTH (Double Pack) (for selective enrichment of Listeria monocytogenes from clinical specimens) (Store below 8º C) 500 gm
201058-08-4 Wang resin Polymere-supported 4- 1g
CHM01H06-10 Cellogel_Myl® (Cellogel supported on polyester film), 5.7 x 10.2 cm. pack
CHM01H16-10 Cellogel_Myl® (Cellogel supported on polyester film), 7 x 23 cm., High Definition pack
GWB-9C8B67 Anti- LOC400451 (hypothetical gene supported by AK075564; BC060873) Antibody
GWB-7BAED9 Anti- LOC400451 (hypothetical gene supported by AK075564; BC060873) Antibody
12262-58-7 Cyclohexanone Perxide Cyclohexanone Perxide 1g


 

GENTAUR Belgium BVBA BE0473327336
Voortstraat 49, 1910 Kampenhout BELGIUM
Tel 0032 16 58 90 45

Fax 0032 16 50 90 45
info@gentaur.com | Gentaur





GENTAUR Ltd.
Howard Frank Turnberry House
1404-1410 High Road
Whetstone London N20 9BH
Tel 020 3393 8531 Fax 020 8445 9411
uk@gentaur.com | Gentaur

 

 




GENTAUR France SARL
9, rue Lagrange, 75005 Paris
Tel 01 43 25 01 50

Fax 01 43 25 01 60
RCS Paris B 484 237 888

SIRET 48423788800017

BNP PARIBAS PARIS PL MAUBERT BIC BNPAFRPPPRG

france@gentaur.com | Gentaur

GENTAUR GmbH
Marienbongard 20
52062 Aachen Deutschland
Support Karolina Elandt
Tel: 0035929830070
Fax: (+49) 241 56 00 47 88

Logistic :0241 40 08 90 86
Bankleitzahl 39050000
IBAN lautet DE8839050000107569353
Handelsregister Aachen HR B 16058
Umsatzsteuer-Identifikationsnummer *** DE 815175831
Steuernummer 201/5961/3925
de@gentaur.com | Gentaur

GENTAUR U.S.A
Genprice Inc, Logistics
547, Yurok Circle
San Jose, CA 95123
CA 95123
Tel (408) 780-0908,
Fax (408) 780-0908,
sales@genprice.com

Genprice Inc, Invoices and accounting
6017 Snell Ave, Ste 357
San Jose, CA 95123




GENTAUR Nederland BV
NL850396268B01 KVK nummer 52327027
Kuiper 1
5521 DG Eersel Nederland
Tel:  0208-080893  Fax: 0497-517897
nl@gentaur.com | Gentaur
IBAN: NL04 RABO 0156 9854 62   SWIFT RABONL2U






GENTAUR Spain
tel:0911876558
spain@gentaur.com | Gentaur






ГЕНТАУЪР БЪЛГАРИЯ
ID # 201 358 931 /BULSTAT
София 1000, ул. "Граф Игнатиев" 53 вх. В, ет. 2
Tel 0035924682280 Fax 0035924808322
e-mail: Sofia@gentaur.com | Gentaur
IBAN: BG11FINV91501014771636
BIC: FINVBGSF

GENTAUR Poland Sp. z o.o.


ul. Grunwaldzka 88/A m.2
81-771 Sopot, Poland
TEL Gdansk 058 710 33 44 FAX  058 710 33 48              

poland@gentaur.com | Gentaur

Other countries

Österreich +43720880899

Canada Montreal +15149077481

Ceská republika Praha +420246019719

Danmark +4569918806

Finland Helsset +358942419041

Magyarország Budapest +3619980547

Ireland Dublin+35316526556

Luxembourg+35220880274

Norge Oslo+4721031366

Sverige Stockholm+46852503438

Schweiz Züri+41435006251

US New York+17185132983

GENTAUR Italy
SRL IVA IT03841300167
Piazza Giacomo Matteotti, 6
24122 Bergamo Tel 02 36 00 65 93
Fax 02 36 00 65 94
italia@gentaur.com | Gentaur