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Search for "phosphine-boranes" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.
Architecture and synthesis of P,N-heterocyclic phosphine ligands
- Wisdom A. Munzeiwa,
- Bernard Omondi and
- Vincent O. Nyamori
Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35
- ] were the phosphine boranes were prepared by reacting phosphines with sodium borohydride. Alternatively, the reduction of phosphine oxide byproducts with lithium tetrahydridoaluminate, calcium aluminum hydride, and hydrosilanes can also be used to regenerate the phosphine ligands. Hydrosilane reagents
Graphical Abstract
Scheme 1: Synthesis of pyridylphosphine ligands.
Figure 1: Pyridylphosphine ligands.
Scheme 2: Synthesis of piperidyl- and oxazinylphosphine ligands.
Scheme 3: Synthesis of linear multi-chelate pyridylphosphine ligands.
Scheme 4: Synthesis of chiral acetal pyridylphosphine ligands.
Scheme 5: Synthesis of diphenylphosphine-substituted triazine ligands.
Scheme 6: Synthesis of (pyridine-2-ylmethyl)phosphine ligands.
Scheme 7: Synthesis of diphosphine pyrrole ligands.
Scheme 8: Synthesis of 4,5-diazafluorenylphosphine ligands.
Scheme 9: Synthesis of thioether-containing pyridyldiphosphine ligands starting from ethylene sulfide and dip...
Scheme 10: Synthesis of monoterpene-derived phosphine pyridine ligands.
Scheme 11: Synthesis of N-phenylphosphine-substituted imidazole ligands.
Scheme 12: Synthesis of triazol-4-ylphosphine ligands.
Scheme 13: Synthesis of phosphanyltriazolopyridines and product selectivity depending on the substituents’ eff...
Scheme 14: Synthesis of PTA-phosphine ligands.
Scheme 15: Synthesis of isomeric phosphine dipyrazole ligands by varying the reaction temperature.
Scheme 16: Synthesis of N-tethered phosphine imidazolium ligands (route A) and diphosphine imidazolium ligands...
Scheme 17: Synthesis of {1-[2-(pyridin-2-yl)- (R = CH) and {1-[2-(pyrazin-2-yl)quinazolin-4-yl]naphthalen-2-yl...
Scheme 18: Synthesis of oxazolylindolylphosphine ligands 102.
Scheme 19: Synthesis of pyrrolylphosphine ligands.
Scheme 20: Synthesis of phosphine guanidinium ligands.
Scheme 21: Synthesis of a polydentate aminophosphine ligand.
Scheme 22: Synthesis of quinolylphosphine ligands.
Scheme 23: Synthesis of N-(triazolylmethyl)phosphanamine ligands.
Figure 2: Triazolylphosphanamine ligands synthesized by Wassenaar’s method [22].
Scheme 24: Synthesis of oxazaphosphorines.
Scheme 25: Synthesis of paracyclophane pyridylphosphine ligands.
Scheme 26: Synthesis of triazolylphosphine ligands.
Figure 3: Click-phosphine ligands.
Scheme 27: Ferrocenyl pyridylphosphine imine ligands.
Scheme 28: Synthesis of phosphinooxazolines (PHOX).
Scheme 29: Synthesis of ferrocenylphosphine oxazoles.
Non-metal-templated approaches to bis(borane) derivatives of macrocyclic dibridgehead diphosphines via alkene metathesis
- Tobias Fiedler,
- Michał Barbasiewicz,
- Michael Stollenz and
- John A. Gladysz
Beilstein J. Org. Chem. 2018, 14, 2354–2365, doi:10.3762/bjoc.14.211
- ; crystal structures; homeomorphic isomerization; hydrogenation; in/out isomers; metathesis; phosphine boranes; Introduction We have found that a variety of metal complexes with trans-phosphine ligands of the formula P((CH2)mCH=CH2)3 (1; m = 4–14) undergo threefold interligand ring closing alkene
- phosphine boranes of alkene containing phosphines. The first involves the monophosphorus precursor H3B·P((CH2)6CH=CH2)3 (1·BH3) [31], and the second a diphosphorus precursor in which one of the methylene chains linking the two phosphorus atoms has already been installed. The advantages and limitations of
- dialkyl effect associated with the quaternary centers [52]. Finally, it should be noted that a number of alkene containing phosphine boranes have been employed in metathesis reactions [53][54]. In particular, the tetraalkenyl diphosphine diborane 19·2BH3 in Scheme 10 represents a downsized version of 11
Graphical Abstract
Scheme 1: Syntheses of gyroscope like platinum and rhodium complexes and dibridgehead diphosphines derived th...
Scheme 2: Synthesis and alkene metathesis of the monophosphorus precursor 1·BH3.
Figure 1: The 13C{1H} NMR spectra (CDCl3, 100 MHz) of in,out-2·2BH3, (in,in/out,out)-2·2BH3, 6·2BH3, and the ...
Scheme 3: Synthesis of the diphosphorus precursor 11·2BH3.
Scheme 4: Truncated approaches to the diphosphorus precursor 11·2BH3 from 10.
Scheme 5: Alkene metathesis of the diphosphorus precursor 11·2BH3.
Scheme 6: Schematic comparison of the key alkene metathesis steps in Scheme 2 and Scheme 5.
Scheme 7: Steps that set the in,in/out,out vs in,out stereochemistry of 2·2BH3 in Scheme 2 and Scheme 5.
Scheme 8: Another non-metal-templated approach to dibridgehead diphosphorus compounds.
Scheme 9: Previously synthesized dibridgehead diphosphine diboranes.
Scheme 10: Alkene metathesis of the tetraalkenyldiphosphine diborane 19·2BH3.
Preparation of phosphines through C–P bond formation
- Iris Wauters,
- Wouter Debrouwer and
- Christian V. Stevens
Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106
- ; enantioselectivity; hydrophosphination; organophosphorus chemistry; phosphines; phosphine-boranes; substitution reactions; trivalent phosphorus; Introduction Phosphines are an important class of organophosphorus compounds. They are often used as ligands in metal complex catalysis and they have become a popular
- phosphine boranes 12a via substitution of the chlorine atom with organometallic nucleophiles. This substitution causes an inversion of configuration at the phosphorus center (Scheme 3). Schuman et al. have prepared several dialkenylphosphines using this methodology [40]. Nucleophilic substitution with
- approach are available [22][42][43][44][45][46][47][48]. In recent years methodologies were developed for the asymmetric alkylation. Livinghouse and Wolfe have reported an enantioselective method for the preparation of chiral tertiary phosphine–boranes starting from a racemic secondary phosphine borane
Graphical Abstract
Scheme 1: Synthesis of P-stereogenic phosphines 5 using menthylphosphinite borane diastereomers 2.
Scheme 2: Enantioselective synthesis of chiral phosphines 10 with ephedrine as a chiral auxiliary.
Scheme 3: Chlorophosphine boranes 11a as P-chirogenic electrophilic building blocks.
Scheme 4: Monoalkylation of phenylphosphine borane 15 with methyl iodide in the presence of Cinchona alkaloid...
Scheme 5: Preparation of tetraphosphine borane 19.
Scheme 6: Using chiral chlorophosphine-boranes 11b as phosphide borane 20 precursors.
Scheme 7: Nickel-catalyzed cross-coupling (dppe = 1,2-bis(diphenylphosphino)ethane).
Scheme 8: Pd-catalyzed cross-coupling reaction with organophosphorus stannanes 30.
Scheme 9: Copper iodide catalyzed carbon–phosphorus bond formation.
Scheme 10: Thermodynamic kinetic resolution as the origin of enantioselectivity in metal-catalyzed asymmetric ...
Scheme 11: Ru-catalyzed asymmetric phosphination of benzyl and alkyl chlorides 35 with HPPhMe (36a, PHOX = pho...
Scheme 12: Pt-catalyzed asymmetric alkylation of secondary phosphines 36b.
Scheme 13: Different adducts 43 can result from hydrophosphination.
Scheme 14: Pt-catalyzed asymmetric hydrophosphination.
Scheme 15: Intramolecular hydrophosphination of phosphinoalkene 47.
Scheme 16: Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes 59.
Scheme 17: Preparation of phosphines using zinc organometallics.
Scheme 18: Preparation of alkenylphosphines 71a from alkenylzirconocenes 69 (dtc = N,N-diethyldithiocarbamate,...
Scheme 19: SNAr with P-chiral alkylmethylphosphine boranes 13c.
Scheme 20: Synthesis of QuinoxP 74 (TMEDA = tetramethylethylenediamine).
Scheme 21: Pd-Mediated couplings of a vinyl triflate 76 with diphenylphosphine borane 13e.
Figure 1: Menthone (83) and camphor (84) derived chiral phosphines.
Scheme 22: Palladium-catalyzed cross-coupling reaction of vinyl tosylates 85 and 87 with diphenylphosphine bor...
Scheme 23: Attempt for the enantioselective palladium-catalyzed C–P cross-coupling reaction between an alkenyl...
Scheme 24: Enol phosphates 88 as vinylic coupling partners in the palladium-catalyzed C–P cross-coupling react...
Scheme 25: Nickel-catalyzed cross-coupling in the presence of zinc (dppe = 1,2-bis(diphenylphosphino)ethane).
Scheme 26: Copper-catalyzed coupling of secondary phosphines with vinyl halide 94.
Scheme 27: Palladium-catalyzed cross-coupling of aryl iodides 97 with organoheteroatom stannanes 30.
Scheme 28: Synthesis of optically active phosphine boranes 100 by cross-coupling with a chiral phosphine boran...
Scheme 29: Palladium-catalyzed P–C cross-coupling reactions between primary or secondary phosphines and functi...
Scheme 30: Enantioselective synthesis of a P-chirogenic phosphine 108.
Scheme 31: Enantioselective arylation of silylphosphine 110 ((R,R)-Et-FerroTANE = 1,1'-bis((2R,4R)-2,4-diethyl...
Scheme 32: Nickel-catalyzed arylation of diphenylphosphine 25d.
Scheme 33: Nickel-catalyzed synthesis of (R)-BINAP 116 (dppe = 1,2-bis(diphenylphosphino)ethane, DABCO = 1,4-d...
Scheme 34: Nickel-catalyzed cross-coupling between aryl bromides 119 and diphenylphosphine (25d) (dppp = 1,3-b...
Scheme 35: Stereocontrolled Pd(0)−Cu(I) cocatalyzed aromatic phosphorylation.
Scheme 36: Preparation of alkenylphosphines by hydrophosphination of alkynes.
Scheme 37: Palladium and nickel-catalyzed addition of P–H to alkynes 125a.
Scheme 38: Palladium-catalyzed asymmetric hydrophosphination of an alkyne 128.
Scheme 39: Ruthenium catalyzed hydrophosphination of propargyl alcohols 132 (cod = 1,5-cyclooctadiene).
Scheme 40: Cobalt-catalyzed hydrophosphination of alkynes 134a (acac = acetylacetone).
Scheme 41: Tandem phosphorus–carbon bond formation–oxyfunctionalization of substituted phenylacetylenes 125c (...
Scheme 42: Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkynes 143.
Scheme 43: Hydrophosphination of alkynes 134c catalyzed by ytterbium-imine complexes 145 (hmpa = hexamethylpho...
Scheme 44: Calcium-mediated hydrophosphanylation of alkyne 134d.
Scheme 45: Formation and substitution of bromophosphine borane 151.
Scheme 46: General scheme for a nickel or copper catalyzed cross-coupling reaction.
Scheme 47: Copper-catalyzed synthesis of alkynylphosphines 156.
