cas 143-66-8, Sodium tetraphenylboron | Articles data

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Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes
Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.
Vasu, Dhananjayan,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information
p. 7162 - 7166
(2015/06/08)

Base-free palladium-catalyzed cross-coupling of arylsulfonium salts with sodium tetraarylborates
Palladium-catalyzed cross-coupling reactions of arylsulfonium salts with sodium tetraarylborates were found to proceed smoothly without recourse to an additional base, providing a new, reliable route to biaryls from organosulfur compounds.
Osuka, Atsuhiro,Vasu, Dhananjayan,Yorimitsu, Hideki
p. 3286 - 3291
(2020/10/20)

Ligand-free, atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature
The atom-efficient cross-coupling reaction of sodium tetraarylborates with aryl iodides and bromides was reported. The reaction can be performed directly using a catalytic system composed of palladium chloride, sodium carbonate and methanol (PdCl2/Na2CO3/MeOH) under heat-free conditions at room temperature in an open air conditions. The reactions carried out in an atom-efficient way as 4 equiv of aryl halides coupled effectively with 1 equiv of sodium tetraarylborates to furnish 4 equiv of the corresponding functionalized biaryls in good to excellent yields.
Zhou, Wen-Jun,Wang, Ke-Hu,Wang, Jin-Xian,Gao, Zhi-Rong
experimental part
p. 7633 - 7641
(2010/12/19)

Chemical Properties

Appearance/Colour :white powder
Melting Point: 300 °C
Density: 1.15 g/cm3
Solubility:relatively well soluble in water. A 0.1 M aqueous solution is generally used as reagent.
Storage Temp.:2-8°C
Sensitive: Light Sensitive
Merck: 14,8690
BRN: 3599783
PSA: 0.00000
LogP: 3.06400

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Chemical Properties

Appearance/Colour :white powder

Melting Point: 300 °C

Density: 1.15 g/cm3

Solubility:relatively well soluble in water. A 0.1 M aqueous solution is generally used as reagent.

Storage Temp.:2-8°C

Sensitive: Light Sensitive

Merck: 14,8690

BRN: 3599783

PSA: 0.00000

LogP: 3.06400

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