2013
DOI: 10.1002/ange.201209107
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Perhalogenated Carba‐closo‐dodecaborate Anions as Ligand Substituents: Applications in Gold Catalysis

Abstract: The success of modern transition-metal catalysis is largely due to the availability of a diverse range of ligand frameworks. One of the most universal aspects of ligand design is the strategic attachment of bulky substituents to influence the activity of catalysts. Sterically demanding substituents kinetically protect the active metal center and, at the same time, promote substrate exchange and low coordination, two processes necessary for turnover. Bulky ligand substituents also influence the selectivity of t… Show more

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Cited by 48 publications
(30 citation statements)
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“…The isopropyl-substituted phosphane derivative [1-iPr 2 P-closo-1-CB 11 H 11 ] -(1c) is easily accessible, similar to the chlorinated analogue [1-iPr 2 P-closo-1-CB 11 Cl 11 ] -that was shown to be a valuable ligand for gold catalyzed hydroaminations of alkynes. [18] Contrary to [1-iPr 2 P-closo-1-CB 11 Cl 11 ] -, 1c was found to be sensitive towards oxygen with [1-iPr 2 (O)P-closo-1-CB 11 H 11 ] -(1d) being the oxidation product.…”
Section: Discussionmentioning
confidence: 74%
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“…The isopropyl-substituted phosphane derivative [1-iPr 2 P-closo-1-CB 11 H 11 ] -(1c) is easily accessible, similar to the chlorinated analogue [1-iPr 2 P-closo-1-CB 11 Cl 11 ] -that was shown to be a valuable ligand for gold catalyzed hydroaminations of alkynes. [18] Contrary to [1-iPr 2 P-closo-1-CB 11 Cl 11 ] -, 1c was found to be sensitive towards oxygen with [1-iPr 2 (O)P-closo-1-CB 11 H 11 ] -(1d) being the oxidation product.…”
Section: Discussionmentioning
confidence: 74%
“…[18] In contrast, the P-C bond lengths of 1c are close to the ones that have been reported for 1-iPr 2 P-2-Mecloso-1,2-C 2 B 10 H 10 [d(C cluster -P) = 1.876(6) Å, d(P-C iPr ) = 1.876(8) and 1.863(7) Å] [34] and d(C-P) as well as d(P-O) of 1d are similar to those of the related ortho-carborane…”
Section: Resultsmentioning
confidence: 97%
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“…Catalyst loadings in the ppm range have been reported for a narrow set of gold-catalyzed reactions. [2] Notable examples include the [(NHC)Au I ]-catalyzed (NHC = N-heterocyclic carbene) alkyne hydration, reported by Nolan and co-workers; [3] the [(NHC)Au I ]-catalyzed intramolecular addition of diol to alkyne, reported by Hashmi and co-workers; [4] the hydroamination of alkynes with a hyperhalogenated carba-closo-dodecaborate anionic ligand, reported by Lavallo and co-workers; [5] and the ester assisted hydration of alkynes catalyzed by small gold clusters, reported by Corma and co-workers. [6] In some exceptional cases, even higher turnovers have been achieved but at the cost of employing relatively high temperatures (e.g.…”
mentioning
confidence: 99%
“…[12] We envisioned synthesizing a normal NHC that would be rendered dianionic, as a result of containing two negatively charged and weakly coordinating [13] N-carboranyl substituents ( Figure 1). [12] We envisioned synthesizing a normal NHC that would be rendered dianionic, as a result of containing two negatively charged and weakly coordinating [13] N-carboranyl substituents ( Figure 1).…”
mentioning
confidence: 99%