65881-97-2Relevant academic research and scientific papers
Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane
Yamamoto, Eiji,Izumi, Kiyotaka,Shishido, Ryosuke,Seki, Tomohiro,Tokodai, Noriaki,Ito, Hajime
, p. 17547 - 17551 (2016/11/28)
The first dimesitylboryl substitution of aryl halides with a silylborane bearing a dimesitylboryl group in the presence of alkali-metal alkoxides is described. The reactions of aryl bromides or iodides with Ph2MeSi?BMes2and Na(OtBu) afforded the desired aryl dimesitylboranes in good to high yields and with high borylation/silylation ratios. Selective reaction of the sterically less-hindered C?Br bond of dibromoarenes provided monoborylated products. This reaction was used to rapidly construct a D-π-A aryl dimesityl borane with a non-symmetrical biphenyl spacer.
Synthesis of B/Si bidentate Lewis acids, o-(fluorosilyl)(dimesitylboryl) benzenes, and their fluoride ion affinity
Kawachi, Atsushi,Tani, Atsushi,Shimada, Junpei,Yamamoto, Yohsuke
, p. 4222 - 4223 (2008/09/21)
o-(Fluorosilyl)(dimesitylboryl)benzenes have been prepared as colorless crystals by reacting fluorodimesitylborane with o-(fluorodimethylsilyl)phenyllithium and o-(fluorodiphenylsilyl)phenyllithium. The o-(fluorosilyl)(dimesitylboryl)benzenes serve as B/Si bidentate Lewis acid and efficiently capture fluoride ion from potassium fluoride in the presence of [2.2.2]cryptand or 18-crown-6 in toluene, giving the corresponding μ-fluoro bridged products. The structures were characterized by X-ray crystal structure analysis and multinuclear NMR spectroscopy. Fluoride ion affinities of the o-(fluorosilyl)(dimesitylboryl)benzenes were evaluated in comparison with non-silylated triarylborane. Copyright
Ambiphilic compounds: Synthesis and structure of a phosphane-borane with a flexible diphenyl ether tether
Bebbington, Magnus W. P.,Bouhadir, Ghenwa,Bourissou, Didier
, p. 4483 - 4486 (2008/02/12)
The preparation of desired phosphane-borane 1 involves selective lithiation trapping of 2-bromo-2′-iododiphenyl ether 3 to give bromophosphane 4 followed by a second lithiation/electrophilic trapping to install the boron fragment. The structure of the new
A comparative study of base-free arylcopper reagents for the transfer of aryl groups to boron halides
Sundararaman, Anand,J?kle, Frieder
, p. 134 - 142 (2007/10/03)
A comparative study on the reactivity and selectivity of arylcopper species in reactions with boron halides was performed. Mesitylcopper reacts with BX3 (X=Cl, Br) in toluene at low temperature under highly selective formation of the monosubstituted boranes MesBX2. The dimesitylboranes Mes2BX are gradually formed with a twofold excess of the organocopper reagent at elevated temperature. In contrast, pentafluorophenylcopper shows a tendency for formation of B(C6F5) 3 in reactions with BX3 irrespective of the stoichiometry used, suggesting a strong impact of electronic factors on the selectivity of the aryl transfer reaction. New procedures for the synthesis of the pentafluorophenylboron halides C6 F5BX2 (X=Cl: 57%; X=Br: 62%) and of tris(pentafluorophenyl)borane (80%) and related mixed-substituted triarylboranes from the base-free isolable pentafluorophenylcopper precursor have been developed.
Synthesis and Properties of 1,3,5-Tris(dimesitylboryl)benzene and 1,3-Bis(dimesitylboryl)benzene
Okada, Keiji,Sugawa, Tadashi,Oda, Masaji
, p. 74 - 75 (2007/10/02)
1,3,5-Tris(dimesitylboryl)benzene and 1,3-bis(dimesitylboryl)benzene were synthesized and their conformational analysis including X-ray structure determination of the former was studied; electrochemical properties of these compounds were also examined.
DIMESITYLBORYL COMPOUNDS. V. ARYL, ETHENYL, ALLENYL, PHENYLETHYNYL AND ALLYL DERIVATIVES
Brown, N.M.D.,Davidson, F.,Wilson, J.W.
, p. 1 - 11 (2007/10/02)
Trimesitylborane, five aryldimesitylboranes, ethenyl, allenyl, phenylethynyl and allyldimesitylboranes have been synthesised and characterised by their 1H, 11B and 13C NMR spectra. A set of 13C chemical shift shielding parameters for the dimesitylborynyl group have been obtained which allow the assignment of 13C resonances in meta- and para-substituted aryldimesitylboranes. On the basis of 13C and 11B chemical shift data it is concluded that the unsaturated ligands stabilise these systems by ? electron back-donation to the empty p orbital on boron in the order aryl allenyl alkenyl alkynyl. Allyldimesitylborane does not undergo the expected intramolecular allylic rearrangement in solution at temperatures below 140 deg C.
BORON PHOTOCHEMISTRY XIV. THE DIMESITYLBORYL GROUP AS AN AUXOCHROME IN DYES: THE SYNTHESIS OF para-SUBSTITUTED DIMESITYLBORYLPHENYLAZONAPHTHOL DYES
Glogowski, M. E.,Williams, J.L.R.
, p. 1 - 8 (2007/10/02)
The dimesitylboryl group is a new auxochrome.This group was evaluated by comparison of 4--1-naphthol (III) with 4--1-naphthol (IV) and of the substituted N--1,3-benzenedisulfonamide (VIIIa) with N--1,3-benzenedisulfonamide (VIIIb).The syntheses of 5-hydroxy-8-(4-dimesitylborylphenylazo)-1-naphthyl amine (IX) and α-propionic acid (X) are reported.The visible spectra of the dimesitylboryl-containing dyes and those of the nitro analogs were similar in shape.The spectral shifts of the dimesitylboryl compounds are as great as those of the corresponding nitro analogs.However, the boryl-substituted dyes required a nondonor medium for alkalinity-induced spectral shifts.As an auxochrome the dimesitylboryl group is roughly equivalent to a nitro group.
