Synthesis and characterization of trans-chlorohydridobis(trimethylphosphine)platinum and an investigation of its role in olefin hydration catalysis

Ramprasad, Dorai; Yue, Hong; Marsella, John A.

doi:10.1021/ic00291a021

Cited by 36 publications

(20 citation statements)

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“…The calculated s iso (SO) shielding constants for selected trans-Pt(PMe 3 ) 2 (H)L for which experimental data are available [40][41][42][43][44] (cf. Table S1, ESI †) demonstrate that the calculated s iso (SO) shielding constants are accurate metrics to deploy the ligands L in reliable trans-philicity ladders (trans-philicity sequences).…”

Section: Resultsmentioning

confidence: 99%

NMR probe effects on trans-philicity and trans-influence ladders in square planar Pt(ii) complexes

Tsipis

2020

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

NMR probe effects on trans-philicity and trans-influence ladders in square planar Pt(ii) complexes

Tsipis

2020

New J. Chem.

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“…Palladium(II) salts promote the addition of water to ethylene and unactivated 1-alkenes, but facile β-hydride elimination leads to oxidation and formation of ketones 7. Reports of platinum-catalyzed anti-Markovnikov hydration of 1-hexene8 have not been validated,9 and as such, transition metal-catalyzed alkene hydration has been restricted to electron deficient alkenes such as maleate esters 10…”

Section: Introductionmentioning

confidence: 99%

Gold(I)-catalyzed hydration of allenes

et al. 2009

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“…In the past, Jensen and Trogler reported a catalytic anti-Markovnikov hydration of terminal alkene using platinum catalyst, 4 however, low reproducibility of the reaction was claimed by other research group. 5 Recently, tandem and one-pot conversion of styrene to 2-phenylethanol was reported. 6 Although the optimum condition gave the product in good yield up to 84%, lower yield and selectivity was observed for aliphatic α-alkenes.…”

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confidence: 99%

Trial for anti-Markovnikov Hydration of 1-Decene Using Platinum Complexes Bearing a PBP Pincer Ligand, Inducing Alkene Isomerization and Decomposition of PBP Ligand

Ogawa¹,

Yamashita²

2014

Chem. Lett.

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Mixing of [(PBP)PtCl] complex with 1-decene and H 2 O afforded isomerized alkenes. Deuterium-labeling experiment indicated the catalytically active hydride species for alkene isomerization formed from water and [(PBP)Pt] complex. Reaction of [(PBP)PtNTf 2 ] with H 2 O gave a platinum hydride complex having PNNP ligand with a loss of boron atom, but the resulting complex showed low catalytic activity. Two types of cationic platinum hydride complexes were suggested as active species for alkene isomerization.Linear n-alcohols are produced on industrial scale as precursors of detergents and plasticizers. 1 As found in general organic chemistry textbooks, a consecutive hydroboration and oxidation sequence can afford n-alcohols on a laboratory scale (eq 1). However, stoichiometric use of borane reagents and oxidants is required, preventing industrial application of this transformation. In industry, linear-selective hydroformylation and subsequent hydrogenation is used for the production of homologated n-alcohols (eq 2). 1 Recently, improvement of this process using tandem catalyst systems or relatively cheaper metals are being developed. 2 To synthesize linear n-alcohols from alkene in large scale, a catalytic anti-Markovnikov hydration could be considered an ideal process 3 (eq 3). In the past, Jensen and Trogler reported a catalytic anti-Markovnikov hydration of terminal alkene using platinum catalyst, 4 however, low reproducibility of the reaction was claimed by other research group. 5 Recently, tandem and one-pot conversion of styrene to 2-phenylethanol was reported. 6 Although the optimum condition gave the product in good yield up to 84%, lower yield and selectivity was observed for aliphatic α-alkenes. HBR 2 BR 2 H H 2 O 2 , NaOH OH hydroboration/oxidation ð1Þ CO/H 2 [Rh, Co] H O H OH H 2 hydroformylation/hydrogenation ð2Þ H 2 O OH anti -Markovnikov hydrationTo achieve the anti-Markovnikov hydration of terminal alkene by using transition-metal catalyst, two possible pathways with activation of alkene or water would be expected. 7 The former has been already established as the Wacker process 8 converting alkenes to the corresponding methyl ketones, where an oxygen atom attacks the 2-position of alkenes. Alternatively, activation of water could be another possibility (Scheme 1). 7 The first step is oxidative addition of OH in H 2 O to low-valent metal complex A to generate hydridohydroxido complex B. 9The following insertion of aliphratic α-alkene to the MH bond in B may form a linear alkyl complex C as generally known in transition-metal chemistry. If a subsequent C(sp 3 )OH bondforming reductive elimination from C occurs to produce linear primary alcohol, the starting low-valent complex A would be regenerated to complete the catalytic cycle. The last step, C(sp 3 )OH bond-forming reductive elimination, is relatively rare. All the reported examples of C(sp 3 )OH reductive elimination are limited as the reactions from Pt(IV) and Pd(II) complexes, 10,11 where an initial dissociation of hydroxide and subsequent nucl...

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Synthesis and characterization of trans-chlorohydridobis(trimethylphosphine)platinum and an investigation of its role in olefin hydration catalysis

Cited by 36 publications

References 0 publications

NMR probe effects on trans-philicity and trans-influence ladders in square planar Pt(ii) complexes

NMR probe effects on trans-philicity and trans-influence ladders in square planar Pt(ii) complexes

Gold(I)-catalyzed hydration of allenes

Trial for anti-Markovnikov Hydration of 1-Decene Using Platinum Complexes Bearing a PBP Pincer Ligand, Inducing Alkene Isomerization and Decomposition of PBP Ligand

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