Hydrophilic pyrazine-based phosphane ligands: synthesis and application in asymmetric hydride transfer and H2-hydrogenation of acetophenone

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Abstract

Pyrazine-based hydrophilic phosphanes are useful ligands for the ruthenium- and rhodium-catalyzed hydrogenations of acetophenone under hydride transfer and dihydrogen conditions. The effect of alcohol additives on the catalytic, enantioselective aqueous hydrogenation of acetophenone is examined with the newly developed (R,R)-DAMPYPHOS as the ligand and Rh2(norbornadiene)2Cl2 as the catalyst precursor, giving rise to higher conversions (up to quantitative) and improved enantiomeric excesses (up to 95%) of the formed 1-phenylethanol.
Original languageUndefined
Pages (from-to)1857-1861
Number of pages5
JournalTetrahedron letters
Volume54
Issue number14
DOIs
Publication statusPublished - 2013

Keywords

  • IR-90130
  • METIS-301587

Cite this

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title = "Hydrophilic pyrazine-based phosphane ligands: synthesis and application in asymmetric hydride transfer and H2-hydrogenation of acetophenone",
abstract = "Pyrazine-based hydrophilic phosphanes are useful ligands for the ruthenium- and rhodium-catalyzed hydrogenations of acetophenone under hydride transfer and dihydrogen conditions. The effect of alcohol additives on the catalytic, enantioselective aqueous hydrogenation of acetophenone is examined with the newly developed (R,R)-DAMPYPHOS as the ligand and Rh2(norbornadiene)2Cl2 as the catalyst precursor, giving rise to higher conversions (up to quantitative) and improved enantiomeric excesses (up to 95{\%}) of the formed 1-phenylethanol.",
keywords = "IR-90130, METIS-301587",
author = "N. Nikishkin and Jurriaan Huskens and Willem Verboom",
year = "2013",
doi = "10.1016/j.tetlet.2013.01.108",
language = "Undefined",
volume = "54",
pages = "1857--1861",
journal = "Tetrahedron letters",
issn = "0040-4039",
publisher = "Elsevier",
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Hydrophilic pyrazine-based phosphane ligands: synthesis and application in asymmetric hydride transfer and H2-hydrogenation of acetophenone. / Nikishkin, N.; Huskens, Jurriaan; Verboom, Willem.

In: Tetrahedron letters, Vol. 54, No. 14, 2013, p. 1857-1861.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Hydrophilic pyrazine-based phosphane ligands: synthesis and application in asymmetric hydride transfer and H2-hydrogenation of acetophenone

AU - Nikishkin, N.

AU - Huskens, Jurriaan

AU - Verboom, Willem

PY - 2013

Y1 - 2013

N2 - Pyrazine-based hydrophilic phosphanes are useful ligands for the ruthenium- and rhodium-catalyzed hydrogenations of acetophenone under hydride transfer and dihydrogen conditions. The effect of alcohol additives on the catalytic, enantioselective aqueous hydrogenation of acetophenone is examined with the newly developed (R,R)-DAMPYPHOS as the ligand and Rh2(norbornadiene)2Cl2 as the catalyst precursor, giving rise to higher conversions (up to quantitative) and improved enantiomeric excesses (up to 95%) of the formed 1-phenylethanol.

AB - Pyrazine-based hydrophilic phosphanes are useful ligands for the ruthenium- and rhodium-catalyzed hydrogenations of acetophenone under hydride transfer and dihydrogen conditions. The effect of alcohol additives on the catalytic, enantioselective aqueous hydrogenation of acetophenone is examined with the newly developed (R,R)-DAMPYPHOS as the ligand and Rh2(norbornadiene)2Cl2 as the catalyst precursor, giving rise to higher conversions (up to quantitative) and improved enantiomeric excesses (up to 95%) of the formed 1-phenylethanol.

KW - IR-90130

KW - METIS-301587

U2 - 10.1016/j.tetlet.2013.01.108

DO - 10.1016/j.tetlet.2013.01.108

M3 - Article

VL - 54

SP - 1857

EP - 1861

JO - Tetrahedron letters

JF - Tetrahedron letters

SN - 0040-4039

IS - 14

ER -