Recent advances in the use of tri(2-furyl)germane, triphenylgermane and their derivatives in organic synthesis

Yorimitsu, Hideki; Oshima, Koichiro

doi:10.1016/j.inoche.2004.11.017

Cited by 43 publications

(10 citation statements)

References 56 publications

(13 reference statements)

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“…Other hydrogermanes were also used. Trifurylgermane reacted smoothly to provide stereopure E - 7 in 72% yield. With n Bu 3 GeH, the conversion (50%) was not complete and product 8 was obtained in a lower 40% yield along with 10% of the carbozincation adduct ( 3 ).…”

Section: Resultsmentioning

confidence: 99%

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

et al. 2018

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The regio-and stereoselective addition of germanium and zinc across the CC triple bond of nitrogen-, sulfur-, oxygen-, and phosphorous-substituted terminal and internal alkynes is achieved by reaction with a combination of R 3 GeH and Et 2 Zn. Diagnostic experiments support a radical-chain mechanism and the -zincated vinylgermanes that show exceptional stability are characterized by NMR spectroscopy and X-ray crystallography. The unique feature of this new radical germylzincation reaction is that the C(sp 2)-Zn bond formed remains available for subsequent in situ Cu(I)-or Pd(0)-mediated CC or C-heteroatom bond formation with retention of the double bond geometry. These protocols offer a modular access to elaborated tri-and tetrasubstituted vinylgermanes decorated with heteroatom substituents  to germanium that are useful for the preparation of stereodefined alkenes. Additional data and discussion, experimental details, NMR spectra for new compounds, and X-ray crystal structures (PDF) Crystallographic information files (CIF)

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Section: Resultsmentioning

confidence: 99%

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

et al. 2018

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“…Organogermanium compounds have recently been recognized as useful reagents for organic synthesis. , Unsaturated germanes are of very low toxicity and therefore can serve as alternatives to the organotin compounds . Functionalized alkynylgermanes, in particular, have been useful synthons in cross-coupling reactions 4a-c as well as in cycloaddition of azides 4d-g and synthesis of other organometallic reagents 4h-j and oligosaccharides. 4l,m Germanium-based compounds possessing a π-conjugated system are also considered (along with the respective silicon compounds) to be potential candidates for electronic devices thanks to their photo- and electroluminescent properties …”

Section: Introductionmentioning

confidence: 99%

New Catalytic Route to Alkynylgermanes

2007

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Vinyl-trisubstituted germanes react selectively with terminal alkynes in the presence of compounds containing Ru-H and Ru-Ge bonds with formation of functionalized alkynylgermanes. The reaction opens the first transition metal catalytic route for the preparation of this class of organogermanes, which are useful reagents for organic synthesis. The mechanism elucidated by NMR spectroscopic study of stoichiometric reactions shows that this process is a new catalytic activation of an sp-hybridized C-H bond involving the previously discovered activation of the dC-Ge bond. † Dedicated to Professor Florian Domka on the occasion of his 75th birthday.

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“…[1] Among all radical reactions,p rocesses involving af inal hydrogen atom transfer from at riorganotin hydride have played au nique role in their development towards synthetic applications. [2] Owing to the toxicity of these tin reagents, several alternatives based on molecules possessing aw eakly bound hydrogen atom, for example,Si ÀH, [3] GeÀH, [4] CÀH, [5] SÀH, [6] BÀH, [7] PÀH, [8] or OÀH, [9] have been developed with variable success depending on the applications. [10] These reagents do not, however,o utperform tin hydride in terms of simplicity of use,s ynthetic efficacy,orp rice.…”

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confidence: 99%

Catechols as Sources of Hydrogen Atoms in Radical Deiodination and Related Reactions

et al. 2016

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When used with trialkylboranes, catechol derivatives, which are low-cost and low toxicity, are valuable hydrogen atom donors for radical chain reactions involving alkyl iodides and related radical precursors. The system 4-tert-butylcatechol/triethylborane has been used to reduce a series of secondary and tertiary iodides, a xanthate, and a thiohydroxamate ester. Catechol derivatives are right in the optimal kinetic window for synthetic applications, as demonstrated by highly efficient radical cyclizations. Cyclizations leading to the formation of quaternary centers can be performed in an all-at-once process (no slow addition of the hydrogen atom donor) at standard concentrations. The H-donor properties of catechol derivatives can be fine-tuned by changing their substitution pattern. In slow radical cyclization processes, an enhanced ratio of cyclized/uncyclized products was obtained by using 3-methoxycatechol instead of 4-tert-butylcatechol.

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Recent advances in the use of tri(2-furyl)germane, triphenylgermane and their derivatives in organic synthesis

Cited by 43 publications

References 56 publications

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

New Catalytic Route to Alkynylgermanes

Catechols as Sources of Hydrogen Atoms in Radical Deiodination and Related Reactions

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