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HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech Hebei ProvinceShijiazhuang 050031, China Website: http://www.sundia.com Page 1 of 24 List of Organic Synthesis & Reaction 1: Metal-catalyzed Reactions: 1.1 Heck Reaction: Example: 1.2 Suzuki Reaction: Example 1: Example 2: 1.3 Negishi Reaction: Example: 1.4 Sonogashira Reaction: Example:

1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

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Page 1: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 1 of 24

List of Organic Synthesis & Reaction

1: Metal-catalyzed Reactions:

1.1 Heck Reaction:

Example:

1.2 Suzuki Reaction:

Example 1:

Example 2:

1.3 Negishi Reaction:

Example:

1.4 Sonogashira Reaction:

Example:

Page 2: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 2 of 24

1.5 Stille Reaction:

Example:

1.6 Buchwald-Hartwig Reaction:

Example 1:

Example 2:

Example 3:

1.7 Ullmann Reaction:

Example:

1.8 Carbonyl-extrusion Reaction:

Example 1:

Page 3: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 3 of 24

Example 2:

1.8 Grubbs Reaction:

Example:

1.9 Catalytic Hydrogenation:

2: Mitsunobu Reaction:

2.1 Inversion for Configuration of Alcohols:

Example:

Page 4: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 4 of 24

2.2 Etherification:

Example:

2.3 Amination:

Example:

2.4 Sulfurization:

Example:

2.5 Halogenation:

Example:

3: Preparation & Protection of amino groups:

3.1 Curtius Rearrangement:

Example:

Page 5: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 5 of 24

3.2 Hofmann Degradation:

Example:

3.3 Reduction of Azides:

Example:

3.4 Substitution of Aminos:

Example:

3.5 Protection of amino groups:

Example:

Page 6: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 6 of 24

4: Synthesis of Chiral α-amino acids:

Example 1:

Example 2:

Example 3:

5: Synthesis of Amide:

Page 7: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 7 of 24

Example 1:

Example 2:

Example 3:

6: Synthesis of Cyanide:

Page 8: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 8 of 24

Example 1:

Dehydrant: P2O5, POCl3, SOCl2, PCl5, TFAA, CH3SO2Cl, TiCl4, etc.

Example 2:

Example 3:

7: Synthesis of Alcohols (Chiral Alcohols) & Phenols and

Hydroxy-Protection:

Example 1:

Reductant: LAH, NaBH4, BH3, Fe-HOAc, Al(OEt)3, etc.

Example 2 (Grignard Reaction):

Page 9: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 9 of 24

Example 3:

Example 4:

Example 5:

Example 6 (Asymmetric Synthesis):

Example 7 (De-Me):

Reagent: HI, HBr, HCl, BX3, AlCl3, TMSI, Py.HCl, etc.

Example 8 (Hydroxy-protection):

Page 10: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 10 of 24

TMS-, TBDMS-, TBDPS-, TIPS-, Bn-, PMB-, THP-, MOM-, EE-, SEM-, Ac-, Bz-, etc.

8: Synthesis of Sulfonyl Chloride & Thioalcohol:

Example 1:

Example 2:

Example 3:

Example 4:

Example 5:

Example 6:

Page 11: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 11 of 24

Example 7:

9: Synthesis of Urea & Thiourea:

Example 1 (Urea):

Example 2 (Thiourea):

Example 3 (Lawesson's reagent):

Page 12: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 12 of 24

Example 4 (P2S5):

10: Synthesis of Aldehydes and Ketones:

Example 1 (Jones Oxidation & PCC, PDC and MnO2 Oxidation):

Example 2 (Swern Oxidation):

Example 3 (TEMPO):

Example 4 (Dess-Martin Oxidation & IBX Oxidation):

Page 13: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 13 of 24

Example 5 (Kornblum Oxidation, Sommelet Oxidation, Hass Oxidation & Kröhnke

Oxidation):

Example 6:

Example 7:

Example 8:

Example 9:

Example 10:

Page 14: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 14 of 24

Example 11:

Example 12 (Vilsmeyer):

Example 12 (Reimer-Tiemann):

Example 13 (Friedel-Crafts):

Example 14 (Dieckmann):

Page 15: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 15 of 24

10: Synthesis of Carboxylic Acids & Carboxylic Esters, Nitro

Compounds, Halogen Compounds:

10.1 Carboxylic Acids:

Example:

10.2 Carboxylic Ester:

Example:

10.3 Nitro Compounds:

10.4 Halogen Compounds:

Example 1:

Page 16: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 16 of 24

Example 2:

Example 3:

Example 4:

11: Synthesis of Indoles:

Example 1:

Example 2:

Page 17: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 17 of 24

12: Synthesis of Quinolines and Isoquinolines:

Example 1:

Example 2:

Example 3:

13: Synthesis of Triazine, Pyrimidines, Pyrazines and Pyridines:

Example 1:

Example 2:

Page 18: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 18 of 24

Example 3:

14: Synthesis of Heterocyclic Aromatics:

Example 1:

Example 2:

Example 3:

Example 4:

Page 19: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 19 of 24

Example 5:

16: Synthesis of Spiro-compounds:

Example 1:

Example 2:

Page 20: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 20 of 24

16: Synthesis of Bridged-ring Compounds:

Example 1:

Example 2:

Example 3:

Page 21: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 21 of 24

Example 4:

16: Synthesis of Saccharides:

Example 1:

Page 22: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 22 of 24

Example 2:

Example 3:

Page 23: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 23 of 24

16: Synthesis of Deuterium Compounds:

Example:

17: Synthesis of Organophosphorus Compounds:

Page 24: 1: Metal-catalyzed Reactions · Title: Sundia MediTech Company, Ltd.(サンディア メディテック カンパニー)社 合成反応の一例 Author: ナミキ商事株式会社

HebeiSundia MediTech Company Ltd. 238 Changjiang Road, Shijiazhuang Hi-tech

Hebei Province,Shijiazhuang 050031, China

Website: http://www.sundia.com

Page 24 of 24

Example:

18: Semi Synthesis of Natural Products:

Example: