CN102146020B - Method for synthesizing 1,3-diphenyl-1-propanol compound - Google Patents

Method for synthesizing 1,3-diphenyl-1-propanol compound Download PDF

Info

Publication number
CN102146020B
CN102146020B CN 201010107852 CN201010107852A CN102146020B CN 102146020 B CN102146020 B CN 102146020B CN 201010107852 CN201010107852 CN 201010107852 CN 201010107852 A CN201010107852 A CN 201010107852A CN 102146020 B CN102146020 B CN 102146020B
Authority
CN
China
Prior art keywords
phenylbenzene
synthetic method
propanol compound
phenylethyl alcohol
alkali
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CN 201010107852
Other languages
Chinese (zh)
Other versions
CN102146020A (en
Inventor
孙凯
杨健
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Changzhou Jiubang Pharmaceutical Co.,Ltd.
Original Assignee
Jilin 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 Jilin University filed Critical Jilin University
Priority to CN 201010107852 priority Critical patent/CN102146020B/en
Publication of CN102146020A publication Critical patent/CN102146020A/en
Application granted granted Critical
Publication of CN102146020B publication Critical patent/CN102146020B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a method for synthesizing a 1,3-diphenyl-1-propanol compound, belonging to a method for synthesizing a compound. P-substituted 1-phenyl ethanol and p-substituted benzyl alcohol are used as raw materials, wherein R and R' are hydrogen atoms, halogen atoms Cl, Br, alkyl and alkoxy, and the adding ratio of the substituted 1-phenyl ethanol to the substituted benzyl alcohol is1: (1-2). The method comprises the following steps of: sequentially adding a dry catalyst, alkali, substituted1-phenyl ethanol and substituted benzyl alcohol into an anhydrous solvent under the condition of nitrogen, placing a reactor into an oil bath of 125 to 135 DEG C, and stirring for 8 to 24 hours; cooling, neutralizing the reaction solution, performing extraction by using ethyl acetate, andconcentrating the extract in vacuum till no ethyl acetate smell; and performing chromatographic purification by using a positive silica gel column of 100 to 200 meshes. The invention has the advantages of simple, convenient and feasible method, low production cost, reduced difficulty of purification and post treatment and weakened influence on the environment.

Description

A kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound
Technical field
The invention belongs to a kind of synthetic method of compound, specifically refer to secondary alcohol and primary alconol cross-coupling reaction.
Background technology
1,3-phenylbenzene-1-propanol compound is as shown in the formula A, wherein Ar 1, Ar 2Be respectively the phenyl of replacement, and derivative B, it is important medicine chemical material, it is at immunosuppression (JACS J.Am.Chem.SOC.1993,115,9925-9938), prevention and treatment nerve degenerative diseases (WO03048142A1), anticoagulation (WO9810763A1), anti-abnormality proliferation (US20030191279), suppress beta-secretase (US2005119329A1), antibiotic (WO2007014885A1), suppress HIV-1 proteolytic enzyme (pharmaceutical chemistry magazine Journal of Medicinal Chemistry, 1997, Vol.40, No.23 3707-3711) etc. is widely used in the medicine in field and intermediate synthetic.Thereby it is convenient, economy, and the exploitation of the synthetic method of environmental protection has caused people's very big concern.
Figure GSA00000036589500011
Studies show that in recent years can be raw material with secondary alcohol and primary alconol based on some metal catalytic, through single step reaction, directly generates 1,3-phenylbenzene-1-propanol compound, shown in reaction formula 1.Because alcohol compound is widely distributed, cheap and easy to get, and the mode that reaction can catalysis, only need a step can generate required product, thereby excited organic chemist's research enthusiasm.
(reaction formula 1)
At present, people have developed multiple synthetic method based on metal catalytic to realize this conversion (a) C.S.Cho, B.T.Kim, H.-S.Kim, T.-J.Kim, S.C.Shim, organo-metallic Organometallics2003,22,3608-3610; B) Shu-Yu Zhang, Yong-Qiang Tu, Chun-An Fan, Yi-Jun Jiang, Lei Shi, Ke Cao, En Zhang, chemistry-European magazine Chem.Eur.J.2008,14,10201-10205; C) R.MartNnez, D.J.RamOn, M.Yus, tetrahedron Tetrahedron 2006,62,8982-8987; D) K.-i.Fujita, C.Asai, T.Yamaguchi, F.Hanasaka, R.Yamaguchi, organic chemistry wall bulletin Org.Lett.2005,7,4017-4019; E) C.S.Cho, W.X.Ren, S.C.Shim, the circular Korean Chem.Soc.2005 of Bull. Korea S Chemical Society, 26,1611-1613; F) Mnica Viciano, Mercedes Sana, Eduardo Peris, organo-metallic Organometallics 2007,26,6050-6054; G) Amparo Prades, Mo ' nica Viciano, Mercedes Sanau ', Eduardo Peris; Organo-metallic Organometallics 2008,27,4254-4259; H) Dinakar Gnanamgari, Chin Hin Leung, Nathan D.Schley, SheenaT.Hilton, Robert H.Crabtree, organic and biological molecular chemistry Org.Biomol.Chem., 2008,6,4442-4445; I) Dinakar Gnanamgari, Effiette L.O.Sauer, Nathan D.Schley, ChaseButler, Christopher D.Incarvito, Robert H.Crabtree, organo-metallic Organometallics 2009,28,321-325; J) Andr é Pontes da Costa, M ó nica Viciano, Mercedes Sana ú, SoniaMerino, Juan Tejeda, Eduardo Peris, Beatriz Royo, organo-metallic Organometallics 2008,27,1305-1309.k) Shimizu K, Sato R, Satsuma A, the international version of applied chemistry Angew.Chem.Int.Ed.2009,48 (22), 3982-3986).However, still there are the following problems has limited the application of this method in 1,3-phenylbenzene-1-propanol compound suitability for industrialized production:
1) such reaction at present is catalyzer with ruthenium (Ru), iridium (Ir), palladium (Pd) and silver (Ag) metalloid all, and it is expensive, has increased reaction cost;
2) some reaction needed is added hydrogen acceptor (as the 1-laurylene) in addition and is promoted the carrying out that react, and has reduced the atomic efficiency of reaction, and also later separation and the purifying for reaction brought very big difficulty;
3) not commercialization of some catalyzer (as RuCl2 (DMSO) 4, etc.) needs specially, is not suitable for industrial production;
4) most of reaction needed add special part (as the azepine carbenes, etc.), so that reaction can carry out smoothly, and obtains selectivity preferably, and these parts often should not obtain, and production cost is quite high;
5) also need to add excessive primary alconol for some reaction and could guarantee selectivity of product preferably, cause waste and the loss of raw material;
6) most of reactions must add stoichiometric alkali and just can receive effect preferably, and this has not only caused very big environmental problem, and produced simultaneously a large amount of alkaline waste liquors have also increased the cost of aftertreatment.
Based on the practical problem of above-mentioned existence, develop simple and easy to doly, with low cost, be suitable for industrializedly 1 more, the synthetic method of 3-phenylbenzene-1-propanol compound seems particularly important.
Summary of the invention
The invention provides a kind of 1, the synthetic method of 3-diaryl-1-propanol compound, to solve the problems referred to above that present synthetic method exists, this compound structure is shown in (I), wherein R and R ' can for hydrogen atom, halogen atom (Cl, Br), alkyl and alkoxyl group.The technical scheme that the present invention takes is:
One, to contain the 1-phenylethyl alcohol (II) that replaces and to be raw material to the benzylalcohol (III) that replaces, wherein R and R ' are hydrogen atom, halogen atom Cl, Br, alkyl and alkoxyl group, and ingredient proportion is 1: 1~2;
Two, under condition of nitrogen gas, with the catalyzer of drying, alkali, 1-phenylethyl alcohol and the benzylalcohol to replacing to replacing, add successively in the anhydrous solvent, reactor is placed 125~135 ℃ oil bath, stir 8~24h; Cooling, neutralization reaction liquid extracts with ethyl acetate, and this extraction liquid of vacuum concentration is to there not being the ethyl acetate flavor; With 100~200 order forward silica gel chromatography, can obtain desired product (I).
One embodiment of the present invention is: to the 1-phenylethyl alcohol that replaces with to preferred 1: 1 of the benzylalcohol ingredient proportion that replaces.
One embodiment of the present invention is: catalyzer is ferrocene, ferrocene methanol and ferrocene formaldehyde, and in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of catalyzer is 1~10mol%.
One embodiment of the present invention is: catalyzer is excellent with ferrocene formaldehyde, and in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of catalyzer is 5mol%.
One embodiment of the present invention is: alkali is Cs 2CO 3, NaOH and KOH, in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of alkali is 10~20mol%.
One embodiment of the present invention is: the preferred NaOH of alkali; In the mole number of corresponding 1-phenylethyl alcohol, preferred 20mol%.
One embodiment of the present invention is: solvent is p-Xylol, o-Xylol and m-xylene, volumetric molar concentration 1.0~2.0.
One embodiment of the present invention is: solvent is excellent with p-Xylol, volumetric molar concentration preferred 1.0.
One embodiment of the present invention is: preferred 130 ℃ of temperature.
One embodiment of the present invention is: the reaction times is excellent with 12h.
Reaction formula of the present invention is as follows:
Figure GSA00000036589500031
(reaction formula 2)
In order to overcome an above-mentioned difficult problem, seek to reduce cost, simplify the operation, economize in raw materials, reduce purifying and post-processing difficulty, particularly reduce the influence to environment as much as possible, complying with the guiding theory of Sustainable development, in conjunction with this laboratory to based on the organic synthesis of cheap metal catalysis and the research interest of catalyzed reaction, we begin to explore 1,3-phenylbenzene-1-propanol compound more economically, and is easy, effectively synthetic method.
In order further to improve productive rate, our high spot reviews the influence to iron class catalyst activity of counter ion and different chemical valency.Continuing FeSO 47H 2O, FeCl 36H 2O, anhydrous FeCl 2, FeCl 24H 2Find in the research of O, ferrocene, ferrocene methanol and ferrocene formaldehyde that the introducing of dicyclopentadienyl can significantly improve productive rate.Commercially available ferrocene for example, ferrocene methanol and ferrocene formaldehyde have than the better catalytic activity of simple molysite, and are excellent with ferrocene formaldehyde, and productive rate can reach 96%.
The invention has the advantages that:
1) with widely distributed, secondary alcohol cheap and easy to get and primary alconol are raw material, in the mode of catalysis, namely can high yield obtain 1,3-diaryl-1-propanol compound through single step reaction, and method is simple, low production cost;
2) ferrocene formaldehyde is commercially produced product, and compares with catalyst system therefor in the past, and price advantage is obvious;
3) need not to add part and hydrogen acceptor, reaction can obtain 96% high yield, greatly reduces production cost, has reduced purifying and post-processing difficulty;
4) only adopt the alkali 10~20mol%NaOH of catalytic amount, reaction is carried out smoothly, weakened the influence to environment;
5) two substrates can react by 1: 1 feed ratio, economize in raw materials.
Embodiment
Embodiment 1
Under nitrogen, with ferrocene 0.1mmol, 18.6mg, Cs 2CO 31.0mmol, 32.6mg, 1-phenyl-ethanol 10.0mmol, 1.22g and phenylcarbinol 15.0mmol, 1.62g adds in the anhydrous m-xylene of 6.7mL successively; Under 125 ℃, stir 8h.Cooling is with NH 4Cl saturated solution neutralization reaction liquid, with ethyl acetate extraction it, and this extraction liquid of vacuum concentration is to there being ethyl acetate flavor; With 100~200 order forward silica gel chromatography, normal hexane: ethyl acetate=40: 1 wash-outs can obtain product 1,3-phenylbenzene-1-propyl alcohol 1.55g, 7.3mmol, productive rate: 73%.
Embodiment 2
Under nitrogen, with ferrocene formaldehyde 0.5mmol, 107.0mg, NaOH2.0mmol, 80.0mg, 1-phenyl-ethanol 10.0mmol, 1.22g and 4-anisole methyl alcohol 10.0mmol, 1.38g adds in the anhydrous p-Xylol of 10.0mL successively; Under 130 ℃, stir 24h.Cooling is with NH 4Cl saturated solution neutralization reaction liquid, with ethyl acetate extraction it, and this extraction liquid of vacuum concentration is to there being ethyl acetate flavor.With 100~200 order forward silica gel chromatography, normal hexane: ethyl acetate=30: 1 wash-outs can obtain product 1-phenyl-3-(4 '-p-methoxy-phenyl)-1-propyl alcohol 2.33g, 9.6mmol, productive rate: 96%.
Embodiment 3
Under nitrogen, with ferrocene methanol 1.0mmol, 216.1mg, KOH1.5mmol, 84.2mg, 1-(4 '-aminomethyl phenyl)-ethanol 10.0mmol, 1.36g and 4-chlorobenzene methanol 20.0mmol, 2.85g adds in the anhydrous o-Xylol of 5.0mL successively.Under 135 ℃, stir 12h; Cooling is with NH 4Cl saturated solution neutralization reaction liquid, with ethyl acetate extraction it, and this extraction liquid of vacuum concentration is to there being ethyl acetate flavor; With 100~200 order forward silica gel chromatography, normal hexane: ethyl acetate=38: 1 wash-outs can obtain product 1-(4 '-aminomethyl phenyl)-3-(4 '-chloro-phenyl-)-1-propyl alcohol 2.11g, 8.1mmol, productive rate: 81%.

Claims (9)

1. the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that comprising the following steps:
One, to contain the 1-phenylethyl alcohol to replacing, its structural formula is
Figure FDA00003314423600011
With benzylalcohol, its structural formula to replacement be
Figure FDA00003314423600012
Be raw material, wherein R and R ' are hydrogen atom, halogen atom Cl, Br, alkyl and alkoxyl group, and ingredient proportion is 1: 1~2;
Two, under condition of nitrogen gas, with the catalyzer of drying, alkali, 1-phenylethyl alcohol and the benzylalcohol to replacing to replacing, add in the anhydrous solvent successively, reactor placed 125~135 ℃ oil bath, stir 8~24h, described catalyzer is ferrocene, ferrocene methanol or ferrocene formaldehyde, and in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of this catalyzer is 1~10mol%; Cooling, neutralization reaction liquid extracts with ethyl acetate, and this extraction liquid of vacuum concentration is to there not being the ethyl acetate flavor; With 100~200 order forward silica gel chromatography, can obtain desired product.
2. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: be 1: 1 to the 1-phenylethyl alcohol that replaces with to the benzylalcohol ingredient proportion that replaces.
3. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: described catalyzer adopts ferrocene formaldehyde, and in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of this catalyzer is 5mol%.
4. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: alkali is Cs 2CO 3, NaOH and KOH, in the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of alkali is 10~20mol%.
5. according to claim 4 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: alkali adopts NaOH; In the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of NaOH is 20mol%.
6. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: described solvent is p-Xylol, o-Xylol and m-xylene, volumetric molar concentration 1.0~2.0.
7. according to claim 6 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: alkali adopts NaOH; In the mole number of corresponding 1-phenylethyl alcohol, the loading capacity of NaOH is 20mol%.
8. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: the oil bath that reactor is placed 130 ℃.
9. according to claim 1 a kind of 1, the synthetic method of 3-phenylbenzene-1-propanol compound is characterized in that: churning time 12h.
CN 201010107852 2010-02-10 2010-02-10 Method for synthesizing 1,3-diphenyl-1-propanol compound Active CN102146020B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201010107852 CN102146020B (en) 2010-02-10 2010-02-10 Method for synthesizing 1,3-diphenyl-1-propanol compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201010107852 CN102146020B (en) 2010-02-10 2010-02-10 Method for synthesizing 1,3-diphenyl-1-propanol compound

Publications (2)

Publication Number Publication Date
CN102146020A CN102146020A (en) 2011-08-10
CN102146020B true CN102146020B (en) 2013-09-18

Family

ID=44420516

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201010107852 Active CN102146020B (en) 2010-02-10 2010-02-10 Method for synthesizing 1,3-diphenyl-1-propanol compound

Country Status (1)

Country Link
CN (1) CN102146020B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011114780A1 (en) * 2011-10-01 2013-04-04 Merck Patent Gmbh Use of propanol and propenol derivatives as antioxidants
CN108017518B (en) * 2018-01-30 2020-10-30 湖北远大富驰医药化工股份有限公司 1, 3-diphenyl-1-propanol and preparation method thereof
CN108129269B (en) * 2018-01-30 2021-05-25 湖北远大富驰医药化工股份有限公司 Method for synthesizing 1, 3-diphenyl-1-propanol from 1, 3-diphenyl-1-propanol and nitromethane
CN109096047B (en) * 2018-08-23 2021-08-10 湖北远大富驰医药化工股份有限公司 Preparation method of (1R) -1, 3-diphenyl-1-propanol
CN112047797B (en) * 2020-09-17 2023-04-07 赣南医学院 Method for preparing alpha-alkyl substituted ketone compound

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5872138A (en) * 1996-09-13 1999-02-16 Merck & Co., Inc. Thrombin inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7179624B2 (en) * 2003-03-25 2007-02-20 Council Of Scientific And Industrial Research Eco friendly process for the preparation of chiral alcohols by asymmetric reduction of prochiral ketones in water using soaked Phaseolus aureus L (green grams)

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5872138A (en) * 1996-09-13 1999-02-16 Merck & Co., Inc. Thrombin inhibitors

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
André Pontes da Costa等.Easy preparation of Cp*-functionalized N-heterocyclic carbenes and their coordination to rhodium and iridium.《Dalton Transactions》.2009,(第35期),第6960-6966页.
André Pontes da Costa等.First Cp*-Functionalized N-Heterocyclic Carbene and Its Coordination to Iridium. Study of the Catalytic Properties.《Organometallics》.2008,第27卷(第6期),第1305-1309页.
Bok Tae Kim等.Ruthenium-Catalyzed One-Pot beta-Alkylation of Secondary Alcohols with Primary Alcohols.《Organometallics》.2003,第22卷(第17期),第3608-3610页.
CATALYSIS》.2008,第350卷(第18期),第2975-2983页. *
Easy preparation of Cp*-functionalized N-heterocyclic carbenes and their coordination to rhodium and iridium;André Pontes da Costa等;《Dalton Transactions》;20090612(第35期);第6960-6966页,尤其是第6963页表格1, *
First Cp*-Functionalized N-Heterocyclic Carbene and Its Coordination to Iridium. Study of the Catalytic Properties;André Pontes da Costa等;《Organometallics》;20080227;第27卷(第6期);第1305-1309页,尤其是1307页表格1 *
Hung Wai Cheung等.Ruthenium-Catalyzed beta-Alkylation of Secondary Alcohols with Primary Alcohols.《ADVANCED SYNTHESIS & CATALYSIS》.2008,第350卷(第18期),第2975-2983页.
Hung Wai Cheung等.Ruthenium-Catalyzed beta-Alkylation of Secondary Alcohols with Primary Alcohols.《ADVANCED SYNTHESIS &amp *
Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes;Shu-Yu Zhang等;《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》;20091013;第48卷(第46期);第8761-8765页 *
Iron-Catalyzed C-C Bond Formation by Direct Functionalization of C-H Bonds Adjacent to Heteroatoms;Zhiping Li等;《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》;20080813;第47卷(第39期);第7497-7500页 *
Ruthenium-Catalyzed One-Pot beta-Alkylation of Secondary Alcohols with Primary Alcohols;Bok Tae Kim等;《Organometallics》;20030719;第22卷(第17期);第3608-3610页 *
Shu-Yu Zhang等.Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes.《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》.2009,第48卷(第46期),第8761-8765页.
Zhiping Li等.Iron-Catalyzed C-C Bond Formation by Direct Functionalization of C-H Bonds Adjacent to Heteroatoms.《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》.2008,第47卷(第39期),第7497-7500页.

Also Published As

Publication number Publication date
CN102146020A (en) 2011-08-10

Similar Documents

Publication Publication Date Title
Zhang et al. Lutidine‐based chiral pincer manganese catalysts for enantioselective hydrogenation of ketones
Van Putten et al. Non‐pincer‐type manganese complexes as efficient catalysts for the hydrogenation of esters
Samec et al. Ruthenium‐Catalyzed Transfer Hydrogenation of Imines by Propan‐2‐ol in Benzene
Hu et al. Nickel‐catalyzed asymmetric hydrogenation of 2‐amidoacrylates
Qiu et al. Efficient ionic‐liquid‐promoted chemical fixation of CO2 into α‐alkylidene cyclic carbonates
Huang et al. Rhodium-catalyzed enantioconvergent isomerization of homoallylic and bishomoallylic secondary alcohols
Göricke et al. Palladium‐Catalyzed Enantioselective Addition of Chiral Metal Enolates to In Situ Generated ortho‐Quinone Methides
Li et al. Gold (I)/Chiral N, N′‐Dioxide–Nickel (II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
Dong et al. Primary alcohols from terminal olefins: formal anti-Markovnikov hydration via triple relay catalysis
Li et al. Bimetallic Gold (I)/Chiral N, N′‐Dioxide Nickel (II) Asymmetric Relay Catalysis: Chemo‐and Enantioselective Synthesis of Spiroketals and Spiroaminals
Zhuo et al. Palladium-catalyzed intermolecular asymmetric allylic dearomatization reaction of naphthol derivatives.
Fogler et al. System with Potential Dual Modes of Metal–Ligand Cooperation: Highly Catalytically Active Pyridine‐Based PNNH–Ru Pincer Complexes
Gnanaprakasam et al. Ruthenium Pincer‐Catalyzed Acylation of Alcohols Using Esters with Liberation of Hydrogen under Neutral Conditions
Brewster et al. Base-free iridium-catalyzed hydrogenation of esters and lactones
Trincado et al. Metal–ligand cooperation in the catalytic dehydrogenative coupling (DHC) of polyalcohols to carboxylic acid derivatives
McGrath et al. A Multicomponent Ni‐, Zr‐, and Cu‐Catalyzed Strategy for Enantioselective Synthesis of Alkenyl‐Substituted Quaternary Carbons
CN102146020B (en) Method for synthesizing 1,3-diphenyl-1-propanol compound
Mori et al. Rapid Access to 3-Aryltetralin Skeleton via C (sp3)–H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C–H Bond in Hydride Shift/Cyclization Sequence
Wang et al. Nickel‐Catalyzed Four‐Component Carbonylation of Ethers and Olefins: Direct Access to γ‐Oxy Esters and Amides
Hu et al. One Step Synthesis of Chiral Olefins via Asymmetric Diamination and their Applications as Ligands for Rhodium (I)‐Catalyzed 1, 4‐Additions
Ko et al. Preparation, characterization, and reactions of [(EDBP) Al (μ-OiPr)] 2, a novel catalyst for MPV hydrogen transfer reactions
US9434665B2 (en) Ruthenium complex and method for preparing methanol and diol
Cuenca et al. Water Compatible Gold (III)‐Catalysed Synthesis of Unsymmetrical Ethers from Alcohols
Liu et al. Reduction of aldehydes and ketones catalyzed by a novel aluminum alkoxide: Mechanistic studies of Meerwein− Ponndorf− Verley reaction
Ho et al. α‐Olefins as Alkenylmetal Equivalents in Catalytic Conjugate Addition Reactions

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20230927

Address after: No. 198, Huacheng Road, Jintan District, Changzhou, Jiangsu 213200

Patentee after: Changzhou Jiubang Pharmaceutical Co.,Ltd.

Address before: 130021 School of pharmacy, Jilin University, 1266 Fujin Road, Jilin, Changchun

Patentee before: Jilin University

TR01 Transfer of patent right