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The use of the sterically demanding IPr* and related ligands in catalysis

(2014) CHEMICAL COMMUNICATIONS. 50(95). p.14926-14937
Author
Organization
Abstract
This account highlights the synthesis and applications of one of the very bulky NHC ligands, IPr* (1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazo-2-ylidene). This ligand and some of its derivatives have been found very effective in several catalytic applications and have enabled the isolation of highly reactive organometallic complexes. More specifically, applications of this ligand in Pd and Ni chemistry have permitted challenging transformations under mild reaction conditions and low catalyst loadings. We report the successes as well as the limitations encountered using transition-metal systems bearing this ligand-type. This report will hopefully serve as a guide to synthetic chemists, providing insights as to when the very sterically demanding IPr* ligand (and its congeners) and in a broader context, very bulky NHC ligands, should be used.
Keywords
N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, ORTHO-SUBSTITUTED BIARYLS, PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM, OLEFIN METATHESIS CATALYSTS, ALKYL AMINO CARBENES, BOND FORMATION, C-N, SULFENATE ANIONS, ARYL CHLORIDES

Citation

Please use this url to cite or link to this publication:

MLA
Izquierdo, Frederic, et al. “The Use of the Sterically Demanding IPr* and Related Ligands in Catalysis.” CHEMICAL COMMUNICATIONS, vol. 50, no. 95, 2014, pp. 14926–37.
APA
Izquierdo, F., Manzini, S., & Nolan, S. (2014). The use of the sterically demanding IPr* and related ligands in catalysis. CHEMICAL COMMUNICATIONS, 50(95), 14926–14937.
Chicago author-date
Izquierdo, Frederic, Simone Manzini, and Steven Nolan. 2014. “The Use of the Sterically Demanding IPr* and Related Ligands in Catalysis.” CHEMICAL COMMUNICATIONS 50 (95): 14926–37.
Chicago author-date (all authors)
Izquierdo, Frederic, Simone Manzini, and Steven Nolan. 2014. “The Use of the Sterically Demanding IPr* and Related Ligands in Catalysis.” CHEMICAL COMMUNICATIONS 50 (95): 14926–14937.
Vancouver
1.
Izquierdo F, Manzini S, Nolan S. The use of the sterically demanding IPr* and related ligands in catalysis. CHEMICAL COMMUNICATIONS. 2014;50(95):14926–37.
IEEE
[1]
F. Izquierdo, S. Manzini, and S. Nolan, “The use of the sterically demanding IPr* and related ligands in catalysis,” CHEMICAL COMMUNICATIONS, vol. 50, no. 95, pp. 14926–14937, 2014.
@article{8168533,
  abstract     = {This account highlights the synthesis and applications of one of the very bulky NHC ligands, IPr* (1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazo-2-ylidene). This ligand and some of its derivatives have been found very effective in several catalytic applications and have enabled the isolation of highly reactive organometallic complexes. More specifically, applications of this ligand in Pd and Ni chemistry have permitted challenging transformations under mild reaction conditions and low catalyst loadings. We report the successes as well as the limitations encountered using transition-metal systems bearing this ligand-type. This report will hopefully serve as a guide to synthetic chemists, providing insights as to when the very sterically demanding IPr* ligand (and its congeners) and in a broader context, very bulky NHC ligands, should be used.},
  author       = {Izquierdo, Frederic and Manzini, Simone and Nolan, Steven},
  issn         = {1359-7345},
  journal      = {CHEMICAL COMMUNICATIONS},
  keywords     = {N-HETEROCYCLIC CARBENE,CROSS-COUPLING REACTIONS,ORTHO-SUBSTITUTED BIARYLS,PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM,OLEFIN METATHESIS CATALYSTS,ALKYL AMINO CARBENES,BOND FORMATION,C-N,SULFENATE ANIONS,ARYL CHLORIDES},
  language     = {eng},
  number       = {95},
  pages        = {14926--14937},
  title        = {The use of the sterically demanding IPr* and related ligands in catalysis},
  url          = {http://dx.doi.org/10.1039/c4cc05289g},
  volume       = {50},
  year         = {2014},
}

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