The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform

George A Olah - One of the best experts on this subject based on the ideXlab platform.

Golam Rasul - One of the best experts on this subject based on the ideXlab platform.

Anthony F Hill - One of the best experts on this subject based on the ideXlab platform.

  • synthetic and structural studies of phosphine coordinated Boronium salts
    Dalton Transactions, 2017
    Co-Authors: Anthony F Hill, Jas S Ward
    Abstract:

    The reaction of BrH2B·SMe2 with primary and secondary phosphines affords a range of Boronium salts of the form [H2B(PR3)2]Br (PR3 = PHCy21; PHPh2, 2; PH2Cy, 3), which have been fully characterised including solid-state determinations. Reactions of bulky tertiary phosphines, e.g., PCy3 and PPh3, with BrH2B·SMe2 do not proceed beyond the phosphine-stabilised bromoborane adducts, however, the smaller tertiary phosphine PMe2Ph readily proceeds to form [H2B(PMe2Ph)2]Br (4). The formation of the unsymmetrical Boronium salts [H2B(PH2Cy)(PHCy2)]Br (5) and [H2B(PHCy2)(PHPh2)]Br (6) was observed by in situ NMR spectroscopy, however, the compounds were found to spontaneously disproportionate to their respective homophosphine Boronium cations, even on prolonged storage in solution at -78 °C. Di- and triphosphines were found to form ring-closed Boronium salts to afford [H2B(κ2-P,P'-diphosphine)]Br (diphosphine = dppe, 7; dcpe, 8; dmpe, 9; dppf, 10; dppf with [AsF6]- counterion, 11; amphos, 12). The analogous methodology with Br2HB·SMe2 proved less generally applicable due to an accessible decomposition pathway being available to Boronium salts bearing primary and secondary phosphines, leading to the formation of phosphonium salts, although [BrHB(dcpe)]Br (13), [BrHB(PMe2Ph)2]Br (14) and [BrHB(amphos)]Br (15) were synthesised with varying degrees of success. Reaction of BrH2B·SMe2 with diphars afforded the Boronium salt [H2B(κ2-P,P'-diphars)]Br (16), which featured two pendant arsine arms. Similarly, triphos was found to react with BrH2B·SMe2 to give [H2B(κ2-P,P'-triphos)]Br (17), which featured a pendant phosphine arm. Substitution of the bromide counter anion with either hexafluoroarsenate or hexfluoroantimonate anions revealed weak hydrogen bonds between the P-H bonds of the Boronium cations and the anions, that appeared through NMR studies to be retained in solution (where hydrogen bonding order was determined to be Br- > [SbF6]-/[AsF6]-). This was further demonstrated by comparison of solid-state structures and solution NMR data of 1 with [H2B(PHCy2)2][SbF6] (18), 4 with [H2B(PMe2Ph)2][AsF6] (19) and 17 with [H2B(triphos)][AsF6] (20).

  • 1 1 bis n methylimidazole 2 trimethylsilyl 1 boracyclohexa 1 4 diene chloride a stable intermediate or tangent en route to 1 n methylimidazole borabenzene
    Journal of the American Chemical Society, 2012
    Co-Authors: Ian A Cade, Anthony F Hill
    Abstract:

    The reaction of 1-chloro-2-(trimethylsilyl)-1-boracylohexa-2,5-diene (1) with N-methylimidazole (NMI) results not in the anticipated borabenzene adduct [(NMI)→BC5H5] (3) but rather the title imidazole-stabilized cyclic Boronium salt [(NMI)2BC5H5SiMe3-2]Cl ([2]Cl), which represents a rare example of a trapped intermediate or possible tangent en route to a neutral borabenzene adduct (3) which may be obtained by heating [2]Cl under vacuum.

  • 1,1-Bis(N-methylimidazole)-2-(trimethylsilyl)-1-boracyclohexa-1,4-diene Chloride: A Stable Intermediate or Tangent en Route to 1-(N-Methylimidazole)borabenzene?
    2012
    Co-Authors: Ian A Cade, Anthony F Hill
    Abstract:

    The reaction of 1-chloro-2-(trimethylsilyl)-1-boracylohexa-2,5-diene (1) with N-methylimidazole (NMI) results not in the anticipated borabenzene adduct [(NMI)→BC5H5] (3) but rather the title imidazole-stabilized cyclic Boronium salt [(NMI)2BC5H5SiMe3-2]Cl ([2]­Cl), which represents a rare example of a trapped intermediate or possible tangent en route to a neutral borabenzene adduct (3) which may be obtained by heating [2]Cl under vacuum

G Surya K Prakash - One of the best experts on this subject based on the ideXlab platform.

Ian A Cade - One of the best experts on this subject based on the ideXlab platform.

  • haloboration of internal alkynes with Boronium and borenium cations as a route to tetrasubstituted alkenes
    ChemInform, 2013
    Co-Authors: James R Lawson, Ewan R Clark, Ian A Cade, Sophia A Solomon, Michael J Ingleson
    Abstract:

    Vinyl boronates are extremely useful precursors, especially for the formation of new C–C bonds by cross-coupling and conjugate addition reactions.1, 2 Although alkyne hydroboration is a powerful synthetic route,3, 4 it is not applicable to the synthesis of trisubstituted vinyl boronates. Thus, alternative regio- and stereospecific methods are needed, particularly for subsequent use in the formation of tetrasubstituted alkenes,5–7 as the production of these important biologically active compounds as single isomers by classical methods is challenging.8 One simple approach to trisubstituted vinyl boronates is the functionalization of internal alkynes by metal-catalyzed 1,2-carboboration9–13 and 1,1-carboboration.14 The introduction of two selectively transformable moieties onto an internal alkyne should enable ready access to tetrasubstituted alkenes by successive cross-coupling reactions. Significant progress has been made in this area, particularly in the dimetalation of internal alkynes to provide two nucleophilic sites of distinct reactivity.15–19 The haloboration of internal alkynes is an attractive alternative to dimetalation, as it generates ambivalent synthetic intermediates that contain both a nucleophilic and an electrophilic position.20 These synthetic intermediates are ideally suited for the diversity-oriented synthesis of tetrasubstituted alkenes. To date, the application of alkyne haloboration with boron trihalides (BX3) has been limited to terminal alkynes, and has proved an effective route to produce trisubstituted alkenes with excellent regio- and stereoselectivity.21–25 The haloboration of internal alkynes is unsuccessful with BCl3, and it is either slow25 or produces isomeric mixtures susceptible to B–C bond cleavage when BBr3 is used.21, 26 Recent calculations found that the haloboration of internal alkynes with BCl3 is endothermic, but as the Lewis acidity of BX3 increases (Cl

  • 1 1 bis n methylimidazole 2 trimethylsilyl 1 boracyclohexa 1 4 diene chloride a stable intermediate or tangent en route to 1 n methylimidazole borabenzene
    Journal of the American Chemical Society, 2012
    Co-Authors: Ian A Cade, Anthony F Hill
    Abstract:

    The reaction of 1-chloro-2-(trimethylsilyl)-1-boracylohexa-2,5-diene (1) with N-methylimidazole (NMI) results not in the anticipated borabenzene adduct [(NMI)→BC5H5] (3) but rather the title imidazole-stabilized cyclic Boronium salt [(NMI)2BC5H5SiMe3-2]Cl ([2]Cl), which represents a rare example of a trapped intermediate or possible tangent en route to a neutral borabenzene adduct (3) which may be obtained by heating [2]Cl under vacuum.

  • 1,1-Bis(N-methylimidazole)-2-(trimethylsilyl)-1-boracyclohexa-1,4-diene Chloride: A Stable Intermediate or Tangent en Route to 1-(N-Methylimidazole)borabenzene?
    2012
    Co-Authors: Ian A Cade, Anthony F Hill
    Abstract:

    The reaction of 1-chloro-2-(trimethylsilyl)-1-boracylohexa-2,5-diene (1) with N-methylimidazole (NMI) results not in the anticipated borabenzene adduct [(NMI)→BC5H5] (3) but rather the title imidazole-stabilized cyclic Boronium salt [(NMI)2BC5H5SiMe3-2]Cl ([2]­Cl), which represents a rare example of a trapped intermediate or possible tangent en route to a neutral borabenzene adduct (3) which may be obtained by heating [2]Cl under vacuum