A straight forward in situ preparation of NHC-substituted phosphapalladacycles

Frey, Guido D.; Schütz, Jan; Herrmann, Wolfgang A.

doi:10.1016/j.jorganchem.2006.01.018

Cited by 38 publications

(19 citation statements)

References 48 publications

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“…Most of the crystal structures of ortho-palladated triaryl-phosphite dimers indicate that in the solid state, the trans isomer crystallizes preferentially, where the two phosphorus atoms are coordinated trans to each other at the palladium center, although in our case the solid state structure of 1a depicts the cis isomer, in contrast to previously reported ortho-palladated triarylphosphane dimer [19,24]. The two Pd atoms in 1a adopt square planar geometry and are connected by two bridging acetate ligands.…”

Section: Ortho-metallated Dimeric Complexcontrasting

confidence: 78%

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Preparation of NHC-substituted phosphitepalladacycles

Tanase

Frey

Herdtweck

et al. 2007

Journal of Organometallic Chemistry

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Section: Ortho-metallated Dimeric Complexcontrasting

confidence: 78%

“…Firstly we used the ''free carbene'' route [19] for highly sterically hindered carbene ligands (Scheme 2), or without isolation of the free carbene the ''in situ'' method, when palladium acetate is used as the starting material [24] (Scheme 3).…”

Section: Nhc-substituted Phosphitepalladacyclesmentioning

confidence: 99%

Preparation of NHC-substituted phosphitepalladacycles

Tanase

Frey

Herdtweck

et al. 2007

Journal of Organometallic Chemistry

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“…However, the use of KOtBu was necessary for the more basic cyclic diaminocarbenes. [119] Palladacycle precatalysts ligated with IMes (139) and IPr (140) were prepared by Nolan and co-workers (Scheme 42), [120] from the isolated carbenes 2 and 4. Bedford et al synthesized (Scheme 43) saturated NHC-ligated phosphite palladacycles 143 and 144 in moderate yields by utilizing pentafluorobenzene carbene adducts 77 and 141 as the NHC source.…”

Section: Cross-couplingmentioning

confidence: 99%

Palladium Complexes of N‐Heterocyclic Carbenes as Catalysts for Cross‐Coupling Reactions—A Synthetic Chemist's Perspective

2007

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Palladium-catalyzed C-C and C-N bond-forming reactions are among the most versatile and powerful synthetic methods. For the last 15 years, N-heterocyclic carbenes (NHCs) have enjoyed increasing popularity as ligands in Pd-mediated cross-coupling and related transformations because of their superior performance compared to the more traditional tertiary phosphanes. The strong sigma-electron-donating ability of NHCs renders oxidative insertion even in challenging substrates facile, while their steric bulk and particular topology is responsible for fast reductive elimination. The strong Pd-NHC bonds contribute to the high stability of the active species, even at low ligand/Pd ratios and high temperatures. With a number of commercially available, stable, user-friendly, and powerful NHC-Pd precatalysts, the goal of a universal cross-coupling catalyst is within reach. This Review discusses the basics of Pd-NHC chemistry to understand the peculiarities of these catalysts and then gives a critical discussion on their application in C-C and C-N cross-coupling as well as carbopalladation reactions.

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“…A number of palladacycles bearing unsaturated NHCs have been found to be efficient catalysts for a variety of C-C coupling reactions [6][7][8][9]. However, the studies on palladacycles with saturated NHC ligands are limited [10].…”

Section: Introductionmentioning

confidence: 99%