Alkynylation of ferrocene by terminal alkynes. Part I. A simple one-step synthesis of ferrocenylacetylenes

Dyadchenko, V. P.; Dyadchenko, M. A.; Okulov, Vladimir N.; Lemenovskii, D. A.

doi:10.1016/j.jorganchem.2010.09.039

Cited by 17 publications

(6 citation statements)

References 19 publications

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“…Generally, moderate yields were given. By using the iron‐mediated strategy, ferrocene was also cross‐dehydrogenatively alkynylated with terminal alkynes . The cheap cobalt complex was also employed in the CDC reaction, achieving β‐sp 2 C−H alkynylation of acrylamides with triisopropylsilylacetylene .…”

Section: Formation Of Spc−sp2c Bondsmentioning

confidence: 99%

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

et al. 2020

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Section: Formation Of Spc−sp2c Bondsmentioning

confidence: 99%

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

et al. 2020

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“…Manipulations with air and moisture sensitive compounds were performed under an argon atmosphere using standard Schlenk techniques. Germylene [(i-Pr) 2 NB(N-2,6-Me 2 C 6 H 3 ) 2 ]Ge, 15 FcCuCR (R = H, 28 Me, 29 Ph, 30 and Fc 31 ), FcCuCCuCFc 32 and fc(CuCPh) 2 33 were prepared according to the literature procedures. All other materials were obtained from commercial suppliers and were used without any additional purification.…”

Section: General Considerationsmentioning

confidence: 99%

Facile activation of alkynes with a boraguanidinato-stabilized germylene: a combined experimental and theoretical study

et al. 2017

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A boraguanidinato-stabilized germylene, [(i-Pr)NB(N-2,6-MeCH)]Ge, reacts with alkynes RC[triple bond, length as m-dash]CR selectively in a 2 : 1 molar ratio to afford 3,4-R,R'-1,2-digermacyclobut-3-enes 1a-e as the products of formal [2 + 2 + 2] cyclization [R/R' = Me/Me (1a), Ph/Ph (1b), Ph/H (1c), t-Bu/H (1d) and Cy/H (1e)]. Ferrocenyl-substituted alkynes react similarly, yielding the corresponding ferrocenylated 3,4-R,R'-1,2-digermacyclobut-3-enes 2a-d [where R/R' = Fc/H (2a), Fc/Me (2b), Fc/Ph (2c), and Fc/Fc (2d); Fc = ferrocenyl]. By contrast, only one of the triple bonds available in conjugated diynes RC[triple bond, length as m-dash]CC[triple bond, length as m-dash]CR is activated with the germylene, while the second one remains intact even in the presence of an excess of the germylene. The exclusive formation of 3,4-R,(C[triple bond, length as m-dash]CR)-1,2-digermacyclobut-3-enes 3a-c [R = Ph (3a), t-Bu(3b), and Fc (3c)] was ascribed to a steric repulsion around the second triple bond. On the other hand, the reaction of the germylene with more flexible dialkyne fc(C[triple bond, length as m-dash]CPh) (fc = ferrocene-1,1'-diyl) proceeded in the expected manner, producing compound 4, where both triple bonds are transformed into 1,2-digermacyclobut-3-ene rings by reaction with four equivalents of the germylene. All compounds were characterized by multinuclear NMR spectroscopy, Raman and IR spectroscopy, and in the case of 1a-c, 2a, 2c, 3a, 3b and 4, also by single-crystal X-ray diffraction analysis. The ferrocenyl substituted compounds were studied by cyclic voltammetry (CV). Finally, the plausible reaction pathway was studied for a model reaction of [(i-Pr)NB(N-2,6-MeCH)]Ge with MeC[triple bond, length as m-dash]CMe using DFT computations.

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“…Next, we focused our attention on the alkynylation of ferrocene 2 H because this reaction could be useful in the preparation of new materials 14. To our knowledge, all the methods available for introducing alkynyl groups at ferrocene cores are indirect or give poor yields 14b. Our method allows the synthesis of 4 aH (67 %) by direct reaction of ferrocene with t BuLi and 1 a (entry 14, Table 1).…”

Section: Methodsmentioning

confidence: 99%

Arylsulfonylacetylenes as Alkynylating Reagents of CH Bonds Activated with Lithium Bases

et al. 2012

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Alkynylation of ferrocene by terminal alkynes. Part I. A simple one-step synthesis of ferrocenylacetylenes

Cited by 17 publications

References 19 publications

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

Cross‐Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes

Facile activation of alkynes with a boraguanidinato-stabilized germylene: a combined experimental and theoretical study

Arylsulfonylacetylenes as Alkynylating Reagents of CH Bonds Activated with Lithium Bases

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