Palladium complex-catalyzed germylation of allylic halides using (germyl)stannanes

Nakano, Taichi; Ono, Kazuyoshi; Senda, Yoshiya; Migita, Toshihiko

doi:10.1016/s0022-328x(00)00620-3

Cited by 7 publications

(1 citation statement)

References 17 publications

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“…137,[142][143][144][145][146][147] However, transition-metal mediated hydrogermylations have also been reported. 146,[148][149][150][151][152][153][154][155][156][157][158] Recently, Blanchard and co-workers established a stereoselective hydrogermylation of α-trifluoromethylated alkynes and employed the germylated compounds in subsequent cross-coupling reactions. 158 Note that hydrosilylation reactions of 3,3,3-trifluoropropene with HSiPh 3 yielding 1,1,1-trifluoropropane-3-triphenylsilane were described before using [Rh(H)-(PEt 3 ) 4 ] as a catalyst.…”

Section: Resultsmentioning

confidence: 99%

Competing reaction pathways of 3,3,3-trifluoropropene at rhodium hydrido, silyl and germyl complexes: C–F bond activation versus hydrogermylation

et al. 2016

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The reaction of the silyl complex [Rh{Si(OEt)}(PEt)] (1) with 3,3,3-trifluoropropene afforded the rhodium complex [Rh(CHCHCF){Si(OEt)}(PEt)] (2) which features a bonded fluorinated olefin. In contrast the rhodium hydrido complex [Rh(H)(PEt)] (3) yielded on treatment with 3,3,3-trifluoropropene in the presence of a base the fluorido complex [Rh(F)(PEt)] (4) together with 1,1-difluoro-1-propene by C-F bond activation. At low temperature the intermediate fac-[Rh(H)(CHCHCF)(PEt)] (5) was detected by NMR spectroscopy. The germyl complex [Rh(GePh)(PEt)] (6) reacted also with 3,3,3-trifluoropropene by C-F bond activation affording again the fluorido complex [Rh(F)(PEt)] (4) as well as the (3,3-difluoroallyl)triphenylgermane 7. The catalytic hydrogermylation of 3,3,3-trifluoropropene in the presence of various germanium hydrides under mild conditions was developed by employing complex 6 as a catalyst. The molecular structures of both germane derivatives (3,3-difluoroallyl)triphenylgermane 7 and 1,1,1-trifluoropropane-3-triphenylgermane 8 were determined by X-ray crystallography.

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Section: Resultsmentioning

confidence: 99%

Competing reaction pathways of 3,3,3-trifluoropropene at rhodium hydrido, silyl and germyl complexes: C–F bond activation versus hydrogermylation

et al. 2016

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Organogermanium Compounds of the Main Group Elements

Zaitsev¹

2023

Organogermanium Compounds

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ChemInform Abstract: Palladium Complex‐Catalyzed Germylation of Allylic Halides Using (Germyl)stannanes.

et al. 2001

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reactions of organo-metal compounds reactions of organo-metal compounds O 0350 -064Palladium Complex-Catalyzed Germylation of Allylic Halides Using (Germyl)stannanes.-(Dimethylphenyl)germylstannane (II) reacts metal-selectively with allylic halides to afford the corresponding allylgermanes in a regio-and stereoselective manner. It reacts more readily than (triethylgermyl)stannane (IX) in these reactions. Previously published results are also given in this work. -(NAKANO, TAICHI; ONO, KAZUYOSHI; SENDA,

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Palladium complex-catalyzed germylation of allylic halides using (germyl)stannanes

Cited by 7 publications

References 17 publications

Competing reaction pathways of 3,3,3-trifluoropropene at rhodium hydrido, silyl and germyl complexes: C–F bond activation versus hydrogermylation

Competing reaction pathways of 3,3,3-trifluoropropene at rhodium hydrido, silyl and germyl complexes: C–F bond activation versus hydrogermylation

Organogermanium Compounds of the Main Group Elements

ChemInform Abstract: Palladium Complex‐Catalyzed Germylation of Allylic Halides Using (Germyl)stannanes.

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