Modification of ligand properties of phosphine ligands for C–C and C–N bond-forming reactions

Morris, David J.; Docherty, Gordon; Woodward, Gary; Wills, Martin

doi:10.1016/j.tetlet.2006.12.027

Cited by 15 publications

(8 citation statements)

References 39 publications

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“…Cross-coupling reactions have been attempted as well. For instance, the C-C and C-N bond-forming reaction was tried by Wills and co-workers, 165 however they showed that the DTBPMB ligand was not the most efficient ligand for making such a coupling. Nevertheless, the Suzuki-Miyaura reaction catalysed by Pd/DTBPMB has been described by McNulty and co-workers.…”

Section: Alkoxycarbonylation Of Vinyl Acetate and Styrenementioning

confidence: 99%

Polymer precursors from catalytic reactions of natural oils

et al. 2012

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Dimethyl 1,19-nonadecanedioate is produced from the methoxycarbonylation of commercial olive, rapeseed or sunflower oils in the presence of a catalyst derived from [Pd 2 (dba) 3 ], bis(ditertiarybutylphosphinomethyl)benzene (BDTBPMB) and methanesulphonic acid (MSA). The diester is then hydrogenated to 1,19-nonadecanediol using Ru/1,1,1-tris-(diphenylphosphinemethyl)ethane (triphos). 1,19-Nonadecadienoic acid is hydrogenated to short chain oligoesters, which can themselves be hydrogenated to 1,19-nonadecanol by hydrogenation in the presence of water.

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Section: Alkoxycarbonylation Of Vinyl Acetate and Styrenementioning

confidence: 99%

Polymer precursors from catalytic reactions of natural oils

et al. 2012

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“…In addition to the carbonylative cross-coupling (see section ), noncarbonylative cross-coupling reactions making use of 1,2-DTBPMB have been attempted as well. For instance, several C–C and C–N bond-forming reactions were investigated by Wills and co-workers in 2007, wherein 1,2-DTBPMB was shown not to be the most efficient ligand for making such a coupling since, e.g., 2,3- O -isopropylidene-2,3-dihydroxy-1,4-bis(di- tert -butylphosphino)butane (DIOP derivative) was more efficient for all studied examples. However, especially in the Sonogashira reaction, quantitative conversion of an electron-poor substrate such as para -iodonitrobenzene was obtained using 1,2-DTBPMB within 6 h (Figure ).…”

Section: Noncarbonylative Reactions With 12-dtbpmbmentioning

confidence: 99%

Magic of Alpha: The Chemistry of a Remarkable Bidentate Phosphine, 1,2-Bis(di-tert-butylphosphinomethyl)benzene

Vondran

Furst

Eastham³

et al. 2021

Chem. Rev.

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The bidentate phosphine ligand 1,2-bis(di-tert-butylphosphinomethyl)benzene (1,2-DTBPMB) has been reported over the years as being one of, if not the, best ligands for achieving the alkoxycarbonylation of various unsaturated compounds. Bonded to palladium, the ligand provides the basis for the first step in the commercial (Alpha) production of methyl methacrylate as well as very high selectivity to linear esters and acids from terminal or internal double bonds. The present review is an overview covering the literature dealing with the 1,2-DTBPMB ligand: from its first reference, its catalysis, including the alkoxycarbonylation reaction and its mechanism, its isomerization abilities including the highly selective isomerizing methoxycarbonylation, other reactions such as cross-coupling, recycling approaches, and the development of improved, modified ligands, in which some tert-butyl ligands are replaced by 2-pyridyl moieties and which show exceptional rates for carbonylation reactions at low temperatures.

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“…Fortunately, Cai's method is not restricted to diarylphosphanes, since dialkylphosphanes were also used in this reaction [26]. In addition, Wills and co-workers reported that, in some cases, the addition of zinc dust improves the yield [27]. Several research groups have adopted the Ni-catalyzed cross-coupling protocol developed by Cai et al for the synthesis of a wide variety of chiral phosphanes: axially chiral Quinazolinap ligand [28,29], P-stereogenic BINAP [30] and other binaphthyl-based phosphane and phosphite ligands [31].…”

Section: Arylation and Vinylation Of Secondary And Primary Phosphanesmentioning

confidence: 99%

Nickel Complexes in C‒P Bond Formation

et al. 2021

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This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry.

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Modification of ligand properties of phosphine ligands for C–C and C–N bond-forming reactions

Cited by 15 publications

References 39 publications

Polymer precursors from catalytic reactions of natural oils

Polymer precursors from catalytic reactions of natural oils

Magic of Alpha: The Chemistry of a Remarkable Bidentate Phosphine, 1,2-Bis(di-tert-butylphosphinomethyl)benzene

Nickel Complexes in C‒P Bond Formation

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