Lithium-aluminate-catalyzed hydrophosphination applications

Research output: Contribution to journalArticle

Abstract

Synthesized, isolated, and characterized by X-ray crystallography and NMR spectroscopic studies, lithium phosphidoaluminate iBu3AlPPh2Li(THF)3 has been tested as a catalyst for hydrophosphination of alkynes, alkenes, and carbodiimides. Based on the collective evidence of stoichiometric reactions, NMR monitoring studies, kinetic analysis, and DFT calculations, a mechanism involving deprotonation, alkyne insertion and protonolysis is proposed for the [iBu3AlHLi]2 aluminate-catalyzed hydrophosphination of alkynes with diphenylphosphine. This study enhances further the development of transition metal free, atom economical homogeneous catalysis using common sustainable main group metals.
LanguageEnglish
Pages12291-12296
Number of pages6
JournalAngewandte Chemie International Edition
Volume58
Issue number35
Early online date1 Jul 2019
DOIs
Publication statusPublished - 26 Aug 2019

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Alkynes
Lithium
Nuclear magnetic resonance
Deprotonation
X ray crystallography
Discrete Fourier transforms
Catalysis
Olefins
Transition metals
Carbodiimides
Alkenes
Atoms
Catalysts
Kinetics
Monitoring
Metals
lithium aluminate

Keywords

  • aluminate
  • homogeneous catalysis
  • hydrophosphination
  • lithium
  • phosphine

Cite this

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title = "Lithium-aluminate-catalyzed hydrophosphination applications",
abstract = "Synthesized, isolated, and characterized by X-ray crystallography and NMR spectroscopic studies, lithium phosphidoaluminate iBu3AlPPh2Li(THF)3 has been tested as a catalyst for hydrophosphination of alkynes, alkenes, and carbodiimides. Based on the collective evidence of stoichiometric reactions, NMR monitoring studies, kinetic analysis, and DFT calculations, a mechanism involving deprotonation, alkyne insertion and protonolysis is proposed for the [iBu3AlHLi]2 aluminate-catalyzed hydrophosphination of alkynes with diphenylphosphine. This study enhances further the development of transition metal free, atom economical homogeneous catalysis using common sustainable main group metals.",
keywords = "aluminate, homogeneous catalysis, hydrophosphination, lithium, phosphine",
author = "Pollard, {Victoria A.} and Allan Young and Ross McLellan and Kennedy, {Alan R.} and Tell Tuttle and Mulvey, {Robert E.}",
year = "2019",
month = "8",
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doi = "10.1002/anie.201906807",
language = "English",
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journal = "Angewandte Chemie International Edition",
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T1 - Lithium-aluminate-catalyzed hydrophosphination applications

AU - Pollard, Victoria A.

AU - Young, Allan

AU - McLellan, Ross

AU - Kennedy, Alan R.

AU - Tuttle, Tell

AU - Mulvey, Robert E.

PY - 2019/8/26

Y1 - 2019/8/26

N2 - Synthesized, isolated, and characterized by X-ray crystallography and NMR spectroscopic studies, lithium phosphidoaluminate iBu3AlPPh2Li(THF)3 has been tested as a catalyst for hydrophosphination of alkynes, alkenes, and carbodiimides. Based on the collective evidence of stoichiometric reactions, NMR monitoring studies, kinetic analysis, and DFT calculations, a mechanism involving deprotonation, alkyne insertion and protonolysis is proposed for the [iBu3AlHLi]2 aluminate-catalyzed hydrophosphination of alkynes with diphenylphosphine. This study enhances further the development of transition metal free, atom economical homogeneous catalysis using common sustainable main group metals.

AB - Synthesized, isolated, and characterized by X-ray crystallography and NMR spectroscopic studies, lithium phosphidoaluminate iBu3AlPPh2Li(THF)3 has been tested as a catalyst for hydrophosphination of alkynes, alkenes, and carbodiimides. Based on the collective evidence of stoichiometric reactions, NMR monitoring studies, kinetic analysis, and DFT calculations, a mechanism involving deprotonation, alkyne insertion and protonolysis is proposed for the [iBu3AlHLi]2 aluminate-catalyzed hydrophosphination of alkynes with diphenylphosphine. This study enhances further the development of transition metal free, atom economical homogeneous catalysis using common sustainable main group metals.

KW - aluminate

KW - homogeneous catalysis

KW - hydrophosphination

KW - lithium

KW - phosphine

U2 - 10.1002/anie.201906807

DO - 10.1002/anie.201906807

M3 - Article

VL - 58

SP - 12291

EP - 12296

JO - Angewandte Chemie International Edition

T2 - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 35

ER -