(E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene

Base Information

• Chemical Name: (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene
• CAS No.: 1091603-83-6
• Molecular Formula: C₂₇H₂₉BO₂
• Molecular Weight: 396.337
• Mol file: 1091603-83-6.mol

Synonyms:(E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene

Chemical Property of (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene

There total 4 articles about (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene 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: 80.0%

ortho-methylphenyl iodide (615-37-2) + diphenyl acetylene (501-65-5) + bis(pinacol)diborane (73183-34-3) → (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene (1091603-83-6)

Guidance literature:

With C₁₈H₃₃P*CuCl; sodium t-butanolate; In toluene; at 80 ℃; for 24h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201310275

Reference yield: 71.0%

2-methylphenyl bromide (95-46-5) + (Z)-2,2'-[1,2-(biphenyl)eth-1-ene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (151416-94-3) → (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene (1091603-83-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; at 60 ℃; for 48h; Inert atmosphere;

DOI:10.1002/anie.200803213

Reference yield:

ortho-methylphenyl iodide (615-37-2) + diphenyl acetylene (501-65-5) + bis(pinacol)diborane (73183-34-3) → (E)-1,2-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)ethene (1091603-83-6) + (Z)-4,4,5,5-tetramethyl-2-(2-(2-phenyl-1-(o-tolyl)vinyl)phenyl)-1,3,2-dioxaborolane + C27H29BO2

Guidance literature:

With palladium diacetate; sodium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In N,N-dimethyl-formamide; at 120 ℃; for 24h; Overall yield = 47 percent; Inert atmosphere;

DOI:10.1021/acscatal.0c02522

upstream raw materials:

2-methylphenyl bromide

(Z)-2,2'-[1,2-(biphenyl)eth-1-ene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

diphenyl acetylene

ortho-methylphenyl iodide