833-81-8 ((E)-1-甲基-1,2二苯基乙烯,trans-alpha-methylstilbene)

反应条件：

1.1 Solvents: Tetrahydrofuran

参考文献：

Triflones (CF3SO2C). Survey of reactivity and synthetic utility

Hendrickson, James B.; et al, Journal of the American Chemical Society, 1974, 96(7), 2275-6

合成路线：1 步

5342-87-0

_100%

反应条件：

1.1 Catalysts: Iodine Solvents: Dichloromethane ; 20 h, 25 °C

参考文献：

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Jereb, Marjan; et al, Acta Chimica Slovenica, 2017, 64(4), 747-762

合成路线：1 步

5342-87-0

_89%

反应条件：

1.1 Catalysts: Sulfuric acid Solvents: Acetic acid ; heated

参考文献：

Friedel-Crafts alkylation of benzene with 1,2-diphenyl-2-propanol, 1-chloro-2,3-diphenylpropane, and 2-methyl-1-phenyl-2-butanol

Khalaf, Ali A.; et al, Journal of the Indian Chemical Society, 2010, 87(5), 595-600

合成路线：1 步

5342-87-0

_65%

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Acetic acid , Water ; 0 °C; 0 °C → rt; 10 min, rt
1.2 Reagents: Sodium carbonate Solvents: Water ; neutralized, rt

参考文献：

Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts

Kindt, Stephanie; et al, Angewandte Chemie, 2016, 55(30), 8744-8747

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium chloride , N,N-Bis(1-methylethyl)-P,P-diphenylphosphinous amide Solvents: Tetrahydrofuran ; 30 min, rt; rt → 65 °C; 24 h, 65 °C

参考文献：

Palladium-catalyzed hydroarylation of alkynes with arylboronic acids

Xu, Xiaoling; et al, Tetrahedron, 2010, 66(13), 2433-2438

合成路线：1 步

_95%

反应条件：

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium , Benzoic acid, 3,3′,3′′-phosphinidynetris-, lithium salt (1:3) Solvents: Toluene , Water ; rt; 2.5 h, 100 °C; 100 °C → rt

参考文献：

Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst

Genin, Emilie; et al, Journal of Organometallic Chemistry, 2004, 689(23), 3820-3830

合成路线：1 步

_95%

反应条件：

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-hydroxydirhodium , Benzoic acid, 3,3′,3′′-phosphinidynetris-, lithium salt (1:3) Solvents: Toluene , Water ; 2.5 h, 100 °C

参考文献：

Efficient synthesis of trisubstituted alkenes in an aqueous-organic system using a versatile and recyclable Rh/m-TPPTC catalyst

Genin, Emilie; et al, Tetrahedron Letters, 2004, 45(21), 4157-4161

合成路线：1 步

948-97-0

_97%

反应条件：

1.1 Catalysts: Sodium triethylborohydride , (SP-5-41)-[2-[[Bis(1,1-dimethylethyl)phosphino-κP]methyl]-6-[(4S)-4-(1,1-dimethy… Solvents: Pentane , Tetrahydrofuran ; 8 h, rt
1.2 Reagents: Oxygen ; rt

参考文献：

Iron Catalyzed Isomerization of α-Alkyl Styrenes to Access Trisubstituted Alkenes

Xu, Songgen; et al, Chinese Journal of Chemistry, 2021, 39(3), 585-589

合成路线：1 步

948-97-0

反应条件：

1.1 Catalysts: Tetrabutylammonium acetate Solvents: Tetrabutylammonium bromide ; 120 °C

参考文献：

Pd Nanoparticle Catalyzed Heck Arylation of 1,1-Disubstituted Alkenes in Ionic Liquids. Study on Factors Affecting the Regioselectivity of the Coupling Process

Calo, Vincenzo; et al, Organometallics, 2003, 22(21), 4193-4197

合成路线：1 步

_95%

反应条件：

1.1 Reagents: Tripotassium phosphate Catalysts: 2456428-19-4 Solvents: Polyethylene glycol ; 2 h, 130 °C

参考文献：

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

Kiani, Mahsa ; et al, Applied Organometallic Chemistry, 2020, 34(11),

合成路线：1 步

_94%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Palladium (nanoparticles) , Copper (nanoparticles) Solvents: Dimethylformamide ; 18 h, 100 °C

参考文献：

Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed micelles and their use in the Heck reaction

Heshmatpour, Felora; et al, Tetrahedron, 2012, 68(14), 3001-3011

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Triallyl cyanurate (reaction products with SBA-15 supported mercaptopropyltrimethoxysilane…) Solvents: Dimethylformamide ; 6 h, 120 °C

参考文献：

Carbon-carbon bond forming reactions: Application of covalently anchored 2,4,6-triallyloxy-1,3,5-triazine (TAT) Pd(II) complex over modified surface of SBA-15 to Heck, Suzuki, Sonogashira and Hiyama cross coupling reactions

Singh, Chandani; et al, Catalysis Communications, 2015, 69, 11-15

合成路线：1 步

_93%

反应条件：

1.1 Reagents: Sodium acetate Catalysts: Palladium (wool-supported) Solvents: Water , Polyethylene glycol ; 80 °C

参考文献：

Biopolymer-metal complex wool-Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media

Wu, Shang; et al, Tetrahedron, 2011, 67(1), 250-256

合成路线：1 步

_92%

反应条件：

1.1 Catalysts: Palladium diacetate , 6A,6B,6C,6D,6E,6F,6G-Heptakis[(aminoiminomethyl)amino]-6A,6B,6C,6D,6E,6F,6G-hept… Solvents: Dimethylformamide , Water ; 15 min, rt
1.2 Reagents: Potassium carbonate ; 30 min, rt
1.3 16 h, 80 °C

参考文献：

The Aminocyclodextrin/Pd(OAc)2 Complex as an Efficient Catalyst for the Mizoroki-Heck Cross-Coupling Reaction

Kanagaraj, Kuppusamy; et al, Chemistry - A European Journal, 2013, 19(43), 14425-14431

合成路线：1 步

_84%

反应条件：

1.1 Reagents: Norbornene , Pinacolborane Catalysts: Tetrakis(trimethylphosphine)iron Solvents: Hexane ; 18 h, 50 °C
1.2 Reagents: Potassium carbonate Catalysts: Palladium diacetate , Tri-tert-butylphosphonium tetrafluoroborate Solvents: 1,4-Dioxane , Water ; 5 h, 100 °C

参考文献：

Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane

Wang, Chao; et al, ACS Catalysis, 2016, 6(11), 7585-7589

合成路线：1 步

14447-41-7

333-27-7

_91%

反应条件：

1.1 Reagents: sec-Butyllithium Solvents: Tetrahydrofuran , Hexane ; 94 s, -50 °C
1.2 10 min, -50 °C
1.3 Reagents: Ammonium chloride Solvents: Water

参考文献：

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis-trans Isomerization in Flow

Lee, Hyune-Jea; et al, Organic Letters, 2021, 23(8), 2904-2910

合成路线：1 步

54486-19-0

_91%

反应条件：

1.1 Reagents: Zinc , Titanium tetrachloride Solvents: Pyridine

参考文献：

Convenient method for the preparation of styrene derivatives by the use of titanium(IV) chloride and zinc

Song, Suk-Zu; et al, Chemistry Letters, 1974, (10), 1161-2

合成路线：1 步

948-99-2

544-97-8

_91%

反应条件：

1.1 Catalysts: Bis(tri-tert-butylphosphine)palladium Solvents: Tetrahydrofuran ; 3 h, 50 °C
1.2 Reagents: Ammonium chloride Solvents: Water ; 0 °C

参考文献：

Pd-catalyzed selective tandem arylation-alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

Shi, Ji-cheng; et al, Journal of Organometallic Chemistry, 2003, 687(2), 518-524

合成路线：1 步

2629-47-2

873-66-5

_90%

反应条件：

1.1 Catalysts: Palladium diacetate Solvents: Acetonitrile
1.2 Reagents: Sodium chloride Solvents: Water

参考文献：

Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air

Matoba, Kazutaka; et al, Journal of Organometallic Chemistry, 1999, 574(1), 3-10

合成路线：1 步

1804967-87-0

_89%

反应条件：

1.1 Catalysts: Lithium bromide , Palladium chloride Solvents: N-Methyl-2-pyrrolidone ; 15 h, 160 °C

参考文献：

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Meng, Guangrong; et al, Angewandte Chemie, 2015, 54(48), 14518-14522

合成路线：1 步

_87%

反应条件：

1.1 Catalysts: Palladium diacetate Solvents: Dimethylformamide ; 60 s, rt → 130 °C; 60 s, 130 °C

参考文献：

Microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts

Li, Jian; et al, Letters in Organic Chemistry, 2013, 10(1), 42-46

合成路线：1 步

41796-38-7

676-58-4

_86%

反应条件：

1.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran ; 12 h, rt
1.2 Reagents: Water ; rt

参考文献：

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

Yang, Zhaozhen; et al, Organic & Biomolecular Chemistry, 2013, 11(13), 2175-2185

合成路线：1 步

_86%

反应条件：

1.1 Reagents: Ethanol , Sodium hydroxide , Bis(pinacolato)diborane Catalysts: Sodium methoxide , Copper , Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ; 2 h, 60 °C
1.2 2 - 6 h, 60 °C

参考文献：

(E)-Alkene Synthesis via Nano-Copper/Homogeneous Palladium Co-Catalysis and Selectivity Amplification

Liu, Shiwen; et al, Asian Journal of Organic Chemistry, 2017, 6(5), 507-511

合成路线：1 步

_61%

反应条件：

1.1 Reagents: Trifluoroacetic acid Catalysts: Tetrabutylammonium fluoride , Bathocuproine , Nickel bromide Solvents: Dimethylformamide ; 12 h, rt

参考文献：

Highly stereoselective synthesis of trans-alkenes via electrochemical Ni-catalyzed hydroarylation of alkynes with aryl iodides

Zhang, Haoxiang; et al, Organic & Biomolecular Chemistry, 2023, 21(25), 5189-5193

合成路线：1 步

873-66-5

_82%

反应条件：

1.1 Reagents: Sodium carbonate , Oxygen Catalysts: Palladium diacetate Solvents: Dimethylformamide ; rt → 50 °C; 3 h, 50 °C

参考文献：

Oxygen-Promoted Pd(II) Catalysis for the Coupling of Organoboron Compounds and Olefins

Jung, Young Chun; et al, Organic Letters, 2003, 5(13), 2231-2234

合成路线：1 步

873-66-5

_45%

反应条件：

1.1 Reagents: Propionic acid , Potassium fluoride Catalysts: Tempo , Palladium diacetate ; 1 h, rt

参考文献：

1,2,3-Trisubstituted Indanes by Highly Diastereoselective Palladium-Catalyzed Oxyarylation of Indenes with Arylboronic Acids and Nitroxides

Kirchberg, Sylvia; et al, Angewandte Chemie, 2010, 49(38), 6877-6880

合成路线：1 步

637-50-3

_76%

反应条件：

参考文献：

The Aminocyclodextrin/Pd(OAc)2 Complex as an Efficient Catalyst for the Mizoroki-Heck Cross-Coupling Reaction

Kanagaraj, Kuppusamy; et al, Chemistry - A European Journal, 2013, 19(43), 14425-14431

合成路线：1 步

2959-74-2

_76%

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Toluene

参考文献：

Allylic and benzylic carbanions substituted by heteroatoms

Biellmann, Jean-Francois; et al, Organic Reactions (Hoboken, 1982, 27,

合成路线：1 步

2959-74-2

_60%

反应条件：

1.1 Reagents: Potassium tert-butoxide Solvents: Benzene

参考文献：

Synthetic applications of phosphoryl-stabilized anions

Wadsworth, William S. Jr., Organic Reactions (Hoboken, 1977, 25,

合成路线：1 步

41796-39-8

676-58-4

_76%

反应条件：

1.1 Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Tetrahydrofuran ; 12 h, rt
1.2 Reagents: Water ; rt

参考文献：

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

Yang, Zhaozhen; et al, Organic & Biomolecular Chemistry, 2013, 11(13), 2175-2185

合成路线：1 步

62673-31-8

_72%

反应条件：

1.1 Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ; 10 min, 60 °C
1.2 Solvents: Tetrahydrofuran ; rt; rt → -28 °C
1.3 Reagents: Chlorotrimethylsilane Solvents: Tetrahydrofuran ; -28 °C; -28 °C → rt; 8 h, rt
1.4 Reagents: Ammonium chloride Solvents: Diethyl ether , Water ; 10 min

参考文献：

Palladium-catalyzed stereoselective synthesis of (E)-stilbenes via organozinc reagents and carbonyl compounds

Wang, Jin-Xian; et al, Advanced Synthesis & Catalysis, 2006, 348, 1262-1270

合成路线：1 步

62673-31-8

_64%

反应条件：

1.1 Reagents: Aluminum chloride Solvents: 1,4-Dioxane ; cooled
1.2 5 min, 0 °C
1.3 Solvents: 1,4-Dioxane ; 5 min; 8 h, 80 °C

参考文献：

Lewis Acid Promoted Carbon-Carbon Double-Bond Formation via Organozinc Reagents and Carbonyl Compounds

Peng, Zhi-Yong; et al, Journal of Organic Chemistry, 2009, 74(17), 6855-6858

合成路线：1 步

108-90-7

_71%