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.
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.
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.
