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Trost ligand

The Trost ligand is a diphosphine used in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from trans-1,2-diaminocyclohexane (DACH) have been developed, such as the (R,R)-DACH-naphthyl ligand derived from 2-diphenylphosphino-1-naphthalenecarboxylic acid. Related bidentate phosphine-containing ligands derived from other chiral diamines and 2-diphenylphosphinobenzoic acid have also been developed for applications in asymmetric synthesis.

Trost ligand
Names
IUPAC name
(1R,2R)-(+)-1,2-diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl)[citation needed]
Preferred IUPAC name
N,N′-[(1R,2R)-cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)benzamide]
Other names
Trost's ligand
Identifiers
  • 138517-61-0 N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9138733 Y
  • 10963521
UNII
  • M4RRX95R5F Y
  • DTXSID80894121
  • InChI=1S/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1 Y
    Key: AXMSEDAJMGFTLR-ZAQUEYBZSA-N Y
  • InChI=1/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1
    Key: AXMSEDAJMGFTLR-ZAQUEYBZBE
  • O=C(N[C@H]4CCCC[C@@H]4NC(=O)c3ccccc3P(c1ccccc1)c2ccccc2)c7ccccc7P(c5ccccc5)c6ccccc6
Properties
C44H40N2O2P2
Molar mass 690.75 g/mol
Appearance White solid
Melting point 136 to 142 °C (277 to 288 °F; 409 to 415 K)
Insoluble; soluble in organic solvents (e.g. acetonitrile, dichloromethane) 1,4-dioxane, methanol, tetrahydrofuran, toluene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
(R,R)-DACH-naphthyl Trost ligand, (1R,2R)-(+)-1,2-diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl)

External links edit

  • Sigma-Aldrich: Trost Ligands
  • Trost Research Group


trost, ligand, diphosphine, used, palladium, catalyzed, trost, asymmetric, allylic, alkylation, other, symmetric, ligands, derived, from, trans, diaminocyclohexane, dach, have, been, developed, such, dach, naphthyl, ligand, derived, from, diphenylphosphino, na. The Trost ligand is a diphosphine used in the palladium catalyzed Trost asymmetric allylic alkylation Other C2 symmetric ligands derived from trans 1 2 diaminocyclohexane DACH have been developed such as the R R DACH naphthyl ligand derived from 2 diphenylphosphino 1 naphthalenecarboxylic acid Related bidentate phosphine containing ligands derived from other chiral diamines and 2 diphenylphosphinobenzoic acid have also been developed for applications in asymmetric synthesis Trost ligand NamesIUPAC name 1R 2R 1 2 diaminocyclohexane N N bis 2 diphenylphosphinobenzoyl citation needed Preferred IUPAC name N N 1R 2R cyclohexane 1 2 diyl bis 2 diphenylphosphanyl benzamide Other names Trost s ligandIdentifiersCAS Number 138517 61 0 N3D model JSmol Interactive imageChemSpider 9138733 YPubChem CID 10963521UNII M4RRX95R5F YCompTox Dashboard EPA DTXSID80894121InChI InChI 1S C44H40N2O2P2 c47 43 37 27 13 17 31 41 37 49 33 19 5 1 6 20 33 34 21 7 2 8 22 34 45 39 29 15 16 30 40 39 46 44 48 38 28 14 18 32 42 38 50 35 23 9 3 10 24 35 36 25 11 4 12 26 36 h1 14 17 28 31 32 39 40H 15 16 29 30H2 H 45 47 H 46 48 t39 40 m0 s1 YKey AXMSEDAJMGFTLR ZAQUEYBZSA N YInChI 1 C44H40N2O2P2 c47 43 37 27 13 17 31 41 37 49 33 19 5 1 6 20 33 34 21 7 2 8 22 34 45 39 29 15 16 30 40 39 46 44 48 38 28 14 18 32 42 38 50 35 23 9 3 10 24 35 36 25 11 4 12 26 36 h1 14 17 28 31 32 39 40H 15 16 29 30H2 H 45 47 H 46 48 t39 40 m0 s1Key AXMSEDAJMGFTLR ZAQUEYBZBESMILES O C N C H 4CCCC C H 4NC O c3ccccc3P c1ccccc1 c2ccccc2 c7ccccc7P c5ccccc5 c6ccccc6PropertiesChemical formula C44H40N2O2P2Molar mass 690 75 g molAppearance White solidMelting point 136 to 142 C 277 to 288 F 409 to 415 K Solubility in water Insoluble soluble in organic solvents e g acetonitrile dichloromethane 1 4 dioxane methanol tetrahydrofuran tolueneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references R R DACH naphthyl Trost ligand 1R 2R 1 2 diaminocyclohexane N N bis 2 diphenylphosphino 1 naphthoyl External links editSigma Aldrich Trost Ligands Trost Research Group nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte nbsp This catalysis article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Trost ligand amp oldid 1165993753, wikipedia, wiki, book, books, library,

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