1,3,2-Dioxaborolane, 2,2'-(phenylethenylidene)bis[4,4,5,5-tetramethyl-

Base Information

• Chemical Name: 1,3,2-Dioxaborolane, 2,2'-(phenylethenylidene)bis[4,4,5,5-tetramethyl-
• CAS No.: 67533-31-7
• Molecular Formula: C20H30B2O4
• Molecular Weight: 356.078
• Mol file: 67533-31-7.mol

Synonyms:

Chemical Property of 1,3,2-Dioxaborolane, 2,2'-(phenylethenylidene)bis[4,4,5,5-tetramethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3,2-Dioxaborolane, 2,2'-(phenylethenylidene)bis[4,4,5,5-tetramethyl-

There total 39 articles about 1,3,2-Dioxaborolane, 2,2'-(phenylethenylidene)bis[4,4,5,5-tetramethyl- 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%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3) → 2,2′-(2-phenylethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (67533-31-7)

Guidance literature:

With p-N,N-dimethylaminobenzoic acid; In octane; at 100 ℃; for 12h; Reagent/catalyst; Solvent; regioselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1021/ol502285s

Reference yield: 90.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + bis(pinacol)diborane (73183-34-3) → 2,2′-(2-phenylethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (67533-31-7)

Guidance literature:

With (CH₃Si(C₆H₄P(C₆H₃(CF₃)2)2)2)Pd(SO₃CF₃); triethylaluminum; In toluene; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja205186k

Reference yield: 86.0%

acetophenone (98-86-2) + bis(pinacol)diborane (73183-34-3) → 2,2′-(2-phenylethene-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (67533-31-7)

Guidance literature:

bis(pinacol)diborane; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; diphenyl(methyl)phosphine; In tetrahydrofuran; at 20 ℃; for 0.166667h; Glovebox; Inert atmosphere;

With sodium formate; In tetrahydrofuran; at 20 ℃; for 0.166667h; Glovebox; Inert atmosphere;

acetophenone; In tetrahydrofuran; at 50 ℃; for 5h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.0c07854

upstream raw materials:

tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methane

benzaldehyde

styrene

bis(pinacol)diborane

Downstream raw materials:

9-Benzylidene-9H-fluorene

(E)-1-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolan-2’-yl)-1,2-diphenylethene

Refernces

• 1、 Wang, Li,Zhang, Binfeng,Zhang, Hua,Zou, Youliang. "Zinc catalysed C3-H borylation of indoles and 1,1-diboration of terminal alkynes". supporting information. p. 11185 - 11188. Retrieved 2021/11/04.
• 2、 Zhang, Bing,Xu, Xin,Tao, Lei,Lin, Zhenyang,Zhao, Wanxiang. "Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities". . p. 9495 - 9505. Retrieved 2021/08/04.