827-52-1 (环己基苯,Phenylcyclohexane)

_100%

反应条件：

1.1 Catalysts: Pyridinium, 1-methyl-, methyl sulfate (1:1) ; 60 min, 50 °C

参考文献：

Synthesis of cyclohexylbenzene using pyridine-based ionic liquid /p-toluenesulfonic acid systems

Zong, Qian-shou; et al, Gaoxiao Huaxue Gongcheng Xuebao, 2014, 28(4), 924-927

合成路线：2 步

132-64-9

参考文献：

Comparative study of alumina- and carbon-supported catalysts for hydrogenolysis and hydrogenation of model compounds and coal-derived liquids

Groot, Cornelis K.; et al, Industrial & Engineering Chemistry Product Research and Development, 1986, 25(4), 522-30

合成路线：1 步

1589-60-2

_100%

反应条件：

1.1 Reagents: Triethylsilane Catalysts: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O) (tin(IV) ion-exchanged or proton-exchanged) Solvents: Dichloromethane ; 1 h, reflux

参考文献：

Deoxygenation of tertiary and secondary benzylic alcohols into alkanes with triethylsilane catalyzed by solid acid tin(IV) ion-exchanged montmorillonite

Tandiary, Michael Andreas; et al, Tetrahedron Letters, 2014, 55(30), 4160-4162

合成路线：1 步

1589-60-2

_85%

反应条件：

1.1 Reagents: Potassium tert-butoxide , 1,1,3,3-Tetramethyldisiloxane , Manganese Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel , 1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: Toluene ; 5 h, 70 °C
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, 70 °C

参考文献：

Nickel-Catalyzed Reductive Deoxygenation of Diverse C-O Bond-Bearing Functional Groups

Cook, Adam; et al, ACS Catalysis, 2021, 11(21), 13337-13347

合成路线：1 步

1589-60-2

_82%

反应条件：

1.1 Reagents: Ammonia

参考文献：

Transformations of phenyl- and benzylcyclobutanes in the presence of aluminum bromide

Finkel'shtein, E. Sh.; et al, Neftekhimiya, 1980, 20(1), 75-81

合成路线：1 步

2387-23-7

_100%

反应条件：

1.1 Catalysts: Aluminum chloride

参考文献：

Friedel-Crafts alkylation reactions of benzene with amide bond containing compounds

Chung, Kun Hoe; et al, Tetrahedron Letters, 1994, 35(18), 2913-14

合成路线：1 步

538-75-0

_100%

反应条件：

1.1 Catalysts: Aluminum chloride Solvents: Benzene

参考文献：

Friedel-Crafts Cyclohexylation of Arenes with 1,3-dicyclohexylcarbodiimide (DCC)

Kim, Jae Nyoung; et al, Tetrahedron Letters, 1994, 35(6), 903-4

合成路线：1 步

771-98-2

_100%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Pinacolborane , 1403650-59-8 Solvents: Benzene-d6 ; 1 atm, 77 K; 3 h, 4 atm, 50 °C

参考文献：

Air-Stable α-Diimine Nickel Precatalysts for the Hydrogenation of Hindered, Unactivated Alkenes

Leonard, Nadia G.; et al, ACS Catalysis, 2018, 8(1), 342-348

合成路线：1 步

771-98-2

_100%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Diisobutylaluminum hydride , Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, iron(2+) salt (2:1) Solvents: Toluene ; 3 h, 2 bar, 20 °C

参考文献：

Alkene Hydrogenations by Soluble Iron Nanocluster Catalysts

Gieshoff, Tim N.; et al, Angewandte Chemie, 2017, 56(13), 3585-3589

合成路线：1 步

771-98-2

_100%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium , Carbon Solvents: Ethanol , Water ; 2 h, 35 psi, 25 °C

参考文献：

Pd-activated carbon catalysts for hydrogenation and Suzuki reactions

Guillen, Elena; et al, Applied Catalysis, 2009, 368(1-2), 113-120

合成路线：1 步

92-52-4

_100%

反应条件：

1.1 Reagents: Isopropanol Catalysts: Nickel Solvents: Isopropanol ; 6 h, 82 °C

参考文献：

Catalyzed transfer hydrogenation by 2-propanol for highly selective PAHs reduction

Philippov, A. A.; et al, Catalysis Today, 2021, 379, 15-22

合成路线：1 步

92-52-4

_100%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol

参考文献：

Preparation of Raney nickel catalysts and their use under conditions comparable with those for platinum and palladium catalysts

Adkins, Homer; et al, Journal of the American Chemical Society, 1948, 70, 695-8

合成路线：1 步

92-52-4

_99%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Tetrahydrofuran ; 250 min, 1 MPa, 343 K

参考文献：

Selective Hydrogenation of Single Benzene Ring in Biphenyl Catalyzed by Skeletal Ni

Lu, Lianhai; et al, ChemCatChem, 2009, 1(3), 369-371

合成路线：1 步

_99%

反应条件：

1.1 Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1) Solvents: Tetrahydrofuran ; 5 min, 0 °C
1.2 Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 90 min, 40 °C; 10 min, 40 °C

参考文献：

Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts

Ghorai, Sujit K.; et al, Organic Letters, 2012, 14(4), 1066-1069

合成路线：1 步

_99%

反应条件：

1.1 Catalysts: (OC-6-43)-[N,N-Bis[(3,5-dimethyl-1H-pyrazol-1-yl-κN2)methyl]-2-pyridinemethanami… Solvents: Tetrahydrofuran ; 30 min, rt; 10 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; rt

参考文献：

Iron(II) complexes with functionalized amine-pyrazolyl tripodal ligands in the cross-coupling of aryl Grignard with alkyl halides

Xue, Fei; et al, Dalton Transactions, 2011, 40(35), 8935-8940

合成路线：1 步

_99%

反应条件：

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 10 min, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents

Nakamura, Masaharu; et al, Journal of the American Chemical Society, 2004, 126(12), 3686-3687

合成路线：1 步

_99%

反应条件：

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 10 min, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents

Nakamura, Masaharu; et al, Journal of the American Chemical Society, 2004, 126(12), 3686-3687

合成路线：1 步

_88%

反应条件：

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine , Zinc chloride Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 1 h
1.2 Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 0 °C; 0.5 h, 50 °C
1.3 Reagents: Ammonium chloride Solvents: Water

参考文献：

Iron-catalyzed chemoselective cross-coupling of primary and secondary alkyl halides with arylzinc reagents

Nakamura, Masaharu; et al, Synlett, 2005, (11), 1794-1798

合成路线：1 步

_85%

反应条件：

1.1 Catalysts: 1H-Benzimidazolium, 1,3-bis[[3,5-bis(1,1-dimethylethyl)-2-hydroxyphenyl]methyl]-… Solvents: Diethyl ether ; 2 min, 0 °C; 120 min, 30 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Efficient cross-coupling of aryl Grignard reagents with alkyl halides by recyclable ionic iron(III) complexes bearing a bis(phenol)-functionalized benzimidazolium cation

Xia, Chong-Liang; et al, Organic & Biomolecular Chemistry, 2013, 11(46), 8135-8144

合成路线：1 步

_99%

反应条件：

1.1 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ; 10 min, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents

Nakamura, Masaharu; et al, Journal of the American Chemical Society, 2004, 126(12), 3686-3687

合成路线：1 步

_98%

反应条件：

参考文献：

Iron-catalyzed chemoselective cross-coupling of primary and secondary alkyl halides with arylzinc reagents

Nakamura, Masaharu; et al, Synlett, 2005, (11), 1794-1798

合成路线：1 步

_95%

反应条件：

1.1 Catalysts: Cobalt chloride (CoCl2) , trans-(-)-N,N,N′,N′-Tetramethyl-1,2-cyclohexanediamine Solvents: Tetrahydrofuran ; 15 min, 25 °C

参考文献：

Cobalt(diamine)-Catalyzed Cross-coupling Reaction of Alkyl Halides with Arylmagnesium Reagents: Stereoselective Constructions of Arylated Asymmetric Carbons and Application to Total Synthesis of AH13205

Ohmiya, Hirohisa; et al, Journal of the American Chemical Society, 2006, 128(6), 1886-1889

合成路线：1 步

100-59-4

_99%

反应条件：

1.1 Reagents: Aluminum chloride Solvents: Tetrahydrofuran ; 0 °C; 45 min, 0 °C; 0 °C → rt
1.2 Catalysts: Dichloro(1,10-phenanthroline-κN1,κN10)cobalt ; 6 h, reflux; reflux → rt
1.3 Reagents: Sodium chloride Solvents: Water

参考文献：

Cobalt-catalyzed cross-coupling reactions of aryl- and alkylaluminum derivatives with (hetero)aryl and alkyl bromides

Dilauro, Giuseppe; et al, Chemical Communications (Cambridge, 2021, 57(81), 10564-10567

合成路线：1 步

100-59-4

_83%

反应条件：

1.1 Catalysts: Stereoisomer of bis[1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazo… Solvents: Tetrahydrofuran ; rt → -30 °C
1.2 1 h, -30 °C → 23 °C
1.3 Reagents: Oxalic acid Solvents: Water

参考文献：

Mechanistic Studies of Catalytic Carbon-Carbon Cross-Coupling by Well-Defined Iron NHC Complexes

Przyojski, Jacob A.; et al, ACS Catalysis, 2015, 5(10), 5938-5946

合成路线：1 步

100-59-4

_72%

反应条件：

1.1 Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, (T-4)-tetrachloroferrate… Solvents: Diethyl ether ; 20 min, 30 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

An efficient and recyclable iron(III)-containing imidazolium salt catalyst for cross-coupling of aryl Grignard reagents with alkyl halides

Yan, ChunHui; et al, Chinese Science Bulletin, 2012, 57(16), 1953-1958

合成路线：1 步

24388-23-6

_99%

反应条件：

1.1 Reagents: tert-Butyllithium Solvents: Pentane , Tetrahydrofuran ; 30 min, -40 °C; -40 °C → 0 °C; 30 min, 0 °C
1.2 Reagents: Dibromo[1,1′-oxybis[ethane]]magnesium Catalysts: Iron(III) acetylacetonate Solvents: Tetrahydrofuran ; 1 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Expedient iron-catalyzed coupling of alkyl, benzyl, and allyl halides with arylboronic esters

Bedford, Robin B.; et al, Chemistry - A European Journal, 2014, 20(26), 7935-7938

合成路线：1 步

931-51-1

108-90-7

_99%

反应条件：

1.1 Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-, chloride (1:… Solvents: Tetrahydrofuran ; 10 min, rt
1.2 Catalysts: Iron(III) acetylacetonate Solvents: Tetrahydrofuran ; 5 min, 25 °C
1.3 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Visible-Light-Promoted Iron-Catalyzed C(sp2)-C(sp3) Kumada Cross-Coupling in Flow

Wei, Xiao-Jing; et al, Angewandte Chemie, 2019, 58(37), 13030-13034

合成路线：1 步

931-51-1

108-90-7

_65%

反应条件：

1.1 Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-, chloride (1:1) Solvents: Tetrahydrofuran ; 70 min, 70 °C
1.2 Catalysts: Ferrous chloride tetrahydrate ; 3 h, 70 °C; 70 °C → rt
1.3 Reagents: Hydrochloric acid Solvents: Pentane , Water

参考文献：

An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides

Perry, Marc C.; et al, Tetrahedron Letters, 2012, 53(33), 4436-4439

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Manganese Catalysts: 2,2′-Bipyridine , Dichloro[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ; 12 h, rt

参考文献：

Nickel-catalyzed C-N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling

Yue, Huifeng; et al, Chemical Science, 2019, 10(16), 4430-4435

合成路线：1 步

_67%

反应条件：

1.1 Reagents: Zinc Catalysts: 2,2′:6′,2′′-Terpyridine , Dibromo[1,1′-(oxy-κO)bis[2-(methoxy-κO)ethane]]nickel Solvents: Dimethylformamide ; 8 h, 60 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Ni-catalyzed deaminative cross-electrophile coupling of katritzky salts with halides via C-N bond activation

Ni, Shengyang; et al, ChemRxiv, 2019, 1, 1-6

合成路线：1 步

474317-61-8

_99%

反应条件：

1.1 Reagents: Methanol , Magnesium Catalysts: Palladium Solvents: Methanol ; 24 h, 20 °C

参考文献：

Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system

Mori, Akinori; et al, Chemistry - A European Journal, 2007, 13(5), 1432-1441

合成路线：1 步

4994-16-5

_99%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Methanol ; 60 min, 1 MPa, 40 °C

参考文献：

Controlled hydrogenation of aromatic compounds by platinum nanowire catalysts

Guo, Zhiqiang; et al, RSC Advances, 2012, 2(8), 3477-3480

合成路线：1 步

4994-16-5

_99%

反应条件：

1.1 Reagents: Hydrogen Catalysts: Platinum , Graphene Solvents: Methanol ; 1 h, 1 bar, 60 °C

参考文献：

Highly-dispersed ultrafine Pt nanoparticles on graphene as effective hydrogenation catalysts

Sheng, Baoqiang; et al, RSC Advances, 2012, 2(13), 5520-5523

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Water ; 40 min, 50 °C

参考文献：

Palladium Nanoparticle-Decorated Porous Metal-Organic-Framework (Zr)@Guanidine: Novel Efficient Catalyst in Cross-Coupling (Suzuki, Heck, and Sonogashira) Reactions and Carbonylative Sonogashira under Mild Conditions

Mohammadi, Leila ; et al, ACS Omega, 2023, 8(18), 16395-16410

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium , Hexakis[μ-[2-amino-1,4-benzenedicarboxylato(2-)-κO1:κO′1]]tetra-μ3-hydroxytetra-… Solvents: Water ; 73 min, 60 °C

参考文献：

Stabilization of Palladium-Nanoparticle-Decorated Postsynthesis-Modified Zr-UiO-66 MOF as a Reusable Heterogeneous Catalyst in C-C Coupling Reaction

Mohammadi, Leila; et al, ACS Omega, 2023, 8(9), 8505-8518

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ; 73 min, 70 °C

参考文献：

Stabilization of Pd NPs over the surface of β-cyclodextrin incorporated UiO-66-NH2 for the C-C coupling reaction

Mohammadi, Leila; et al, RSC Advances, 2023, 13(25), 17143-17154

合成路线：1 步

_97%

反应条件：

1.1 Catalysts: Di-μ-chlorobis(η3-2-propenyl)dipalladium , N1,N1,N2,N2-Tetrakis[(diphenylphosphino)methyl]-1,2-cyclohexanediamine Solvents: Dimethylformamide ; 0.5 h, 25 °C
1.2 Reagents: Potassium carbonate Solvents: Isopropanol ; 6 h, 60 °C

参考文献：

A new tetraphosphine and its application in Pd-catalyzed Suzuki cross-coupling reaction

Zhang, Yu; et al, Youji Huaxue, 2012, 32(4), 790-793

合成路线：1 步

_91%

反应条件：

1.1 Reagents: Potassium tert-butoxide Catalysts: Bis(1,5-cyclooctadiene)nickel , 4,7-Diphenyl-1,10-phenanthroline Solvents: (±)-2-Butanol ; 10 min, rt
1.2 5 h, 60 °C

参考文献：

Suzuki Cross-Couplings of Unactivated Secondary Alkyl Bromides and Iodides

Zhou, Jianrong; et al, Journal of the American Chemical Society, 2004, 126(5), 1340-1341

合成路线：1 步

108-93-0

_97%

反应条件：

1.1 Catalysts: Boron trifluoride etherate

参考文献：

Cyclohexylation of benzene

Saha, Manoranjan; et al, Bangladesh Journal of Scientific and Industrial Research, 1998, 33(4), 532-534

合成路线：1 步

108-93-0

_94%