(Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane

Base Information

• Chemical Name: (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane
• CAS No.: 185989-96-2
• Molecular Formula: C₂₂H₃₃BO₂Si
• Molecular Weight: 368.399
• Mol file: 185989-96-2.mol

Synonyms:(Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane

Chemical Property of (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane

There total 4 articles about (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

1-ethenylcyclohexene (931-49-7) + dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane (185989-96-2)

Guidance literature:

1,1,3,3-tetramethylbutane isonitrile; palladium diacetate; In toluene; Heating;

DOI:10.1016/S0040-4020(99)00444-5

Reference yield: 81.0%

1-ethenylcyclohexene (931-49-7) + dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → (E)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl (phenyl)silane (1565830-16-1) + (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane (185989-96-2)

Guidance literature:

With Au-TiO₂; In dichloromethane; at 25 ℃; for 2h; regioselective reaction;

DOI:10.1021/ol500225x

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) → (Z)-(2-(cyclohex-1-en-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)dimethyl(phenyl)silane (185989-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CH₂Cl₂ / 10 h / 20 °C

2: 94 percent / palladium(II) acetate; 1,1,3,3-tetramethylbutyl isocyanide / toluene / Heating

1,1,3,3-tetramethylbutane isonitrile; palladium diacetate; In dichloromethane; toluene; 1: Substitution / 2: Addition;

DOI:10.1016/S0040-4020(99)00444-5

upstream raw materials:

1-ethenylcyclohexene

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

2,3-dimethyl-2,3-butane diol

(bis(diethylamino)-boranyl)dimethylphenylsilane