Bidentate phosphines of heteroarenes: 1,9-bis(diphenylphosphino)-dibenzothiophene and 4,6-bis(diphenylphosphino)dibenzothiophene

Haenel, Matthias W.; Fieseler, Heike; Jakubik, Dieter; Gabor, Barbara; Goddard, Richard; Krüger, Carl

doi:10.1016/s0040-4039(00)60357-x

Cited by 33 publications

(25 citation statements)

References 17 publications

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“…Reactions of Tris(triethylphosphine)platinum(0) with Dimethyldibenzothiophenes. When 4,6-dimethyldibenzothiophene is prepared by the standard lithiation/methylation method, which involves the lithiation of dibenzothiophene with butyllithium, followed by a methylation with dimethyl sulfate, it contains a mixture of dimethyldibenzothiophenes, among them 4,6-dimethyldibenzothiophene and 1,9-dimethyldibenzothiophene as shown by Haenel et al12c Thus when this mixture was reacted with Pt(0), it did not give the expected thiaplatinacycle 8 . Instead we could only isolate complex 9 (in 10% yield).…”

Section: Resultsmentioning

confidence: 99%

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

et al. 1999

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The reaction of [Pt(PEt3)3], 1, with 3-methylbenzothiophene and 2-methylbenzothiophene afforded the thiaplatinacycles [(Et3P)2Pt(C,S-C9H8S)], 3 and 4, respectively. In the formation of both complexes (Et3P)2Pt has inserted into the C−S bond to the vinylic carbon. Complex 4 rearranges in solution to a dimeric thiaplatinacycle, 5, in which the platinum has moved from lying between the vinylic C−S bond into the aromatic C−S bond. Reaction of 1 with 4-methyldibenzothiophene gave a mixture of isomeric thiaplatinacycles [(Et3P)2Pt(C,S-C13H10S)], 6 and 7. The reaction of 1 with 4,6-dimethyldibenzothiophene containing some 1,9-dimethyldibenzothiophene led to the isolation of complex 9, [(Et3P)2Pt(C,S-C14H12S)]. This is derived from 1,9-dimethyldibenzothiophene, which is a byproduct in the preparation of 4,6-dimethyldibenzothiophene by a metalation pathway. The reaction of 1 with highly pure 4,6-dimethyldibenzothiophene gave the hydride complex, 10, in which (Et3P)2Pt has inserted into the C−H bond at the 3-position. The thiaplatinacycle cis-[(Et3P)2Pt(η2-C,S-C14H12S)], 8, was obtained by reaction of highly pure 4,6-dimethyldibenzothiophene with cis-[PtCl2(PEt3)2] and metallic sodium under hydrogen. X-ray structures of complexes 3, 5, and 9 are reported.

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Section: Resultsmentioning

confidence: 99%

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

et al. 1999

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“…4.5 Hz) in their 1 H NMR spectra corresponding to the methine proton spanned by phosphine groups, along with a singlet assigned to the back methine hydrogen (at 5.86, 5.87, and 5.81 ppm, respectively). The through-space H–P splitting implies that static phosphine groups converged at the front methine hydrogen . The three-dimensional shape of the molecule results in perfectly resolved anisochronous i- propyl methyl and methine groups within each of the iso -propylphosphine substituents (please see the Supporting Information).…”

Section: Results and Discussionmentioning

confidence: 99%

Iridium PC(sp³)P Pincer Complexes with Hemilabile Pendant Arms: Synthesis, Characterization, and Catalytic Activity

2018

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A series of new PC(sp3)P pincer ligands possessing hemilabile alkoxyl side arms as well as their iridium complexes are reported. All new organometallic compounds were structurally characterized including X-ray analysis. The hemilability of the side arms was probed by reactions with CO, revealing the reversible coordination. The catalytic activity of the new complexes was tested by iridium-catalyzed transfer dehydrogenation of alkanes under mild conditions.

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“…A successive procedure of this kind provides a synthetic access to phosphathienoquinones (31)(32) and their carboanalogues [27].…”

Section: Phosphorylation Of Metalated Thiophenesmentioning

confidence: 99%

“…Successive treatment of thiophenes with BuLi, CuI, and diethyl iodomethyl phosphonate has enabled direct introduction of a methylenephosphonate group into the thiophene nucleus (34); the authors noted that the 2-thienylcopper reagents were formed as intermediates [29][30][31][32].…”

Section: Phosphorylation Of Metalated Thiophenesmentioning

confidence: 99%

Phosphorylation of Thiophenes

Ivonin¹,

Tolmachev²,

Пинчук³

2008

COC

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This review deals with synthetic methods, chemical transformations, and some physical properties of thienyland benzothienyl substituted phosphorus compounds bearing P-Het or P-CH 2 -Het bonds.The basic synthetic approaches to these compounds include reactions of metalated thiophenes with phosphorus(III) and (V) halides, phosphorylation of thiophenes in the presence of a mild Lewis acid, use of halogenothiophenes in the Arbuzov reaction, and phosphorylation of thiophenes with phosphorus(III) halides in basic medium. Synthetic approaches to condensed heterocyclic systems of novel types are also considered.Investigation of chemical properties of phosphorylated thiophenes has revealed that, despite the great similarity with phenyl analogues, differences connected to the nature of the heterocycle are observed. The tertiary phosphines bearing at least one thienyl substituent are less active in quaternization and oxidation reactions. At the same time, basic hydrolysis leading to C-P bond cleavage is facilitated, as compared to benzene derivatives.

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Bidentate phosphines of heteroarenes: 1,9-bis(diphenylphosphino)-dibenzothiophene and 4,6-bis(diphenylphosphino)dibenzothiophene

Cited by 33 publications

References 17 publications

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

Iridium PC(sp³)P Pincer Complexes with Hemilabile Pendant Arms: Synthesis, Characterization, and Catalytic Activity

Phosphorylation of Thiophenes

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Bidentate phosphines of heteroarenes: 1,9-bis(diphenylphosphino)-dibenzothiophene and 4,6-bis(diphenylphosphino)dibenzothiophene

Cited by 33 publications

References 17 publications

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

Ring Opening of Methylbenzothiophenes and Methyldibenzothiophenes by Tris(triethylphosphine)platinum(0)

Iridium PC(sp3)P Pincer Complexes with Hemilabile Pendant Arms: Synthesis, Characterization, and Catalytic Activity

Phosphorylation of Thiophenes

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Product

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Iridium PC(sp³)P Pincer Complexes with Hemilabile Pendant Arms: Synthesis, Characterization, and Catalytic Activity