Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

Gimbert, Carolina; Moreno‐Mañas, Marcial; Perez, Elisabet; Vallribera, Adelina

doi:10.1016/j.tet.2007.05.088

Cited by 48 publications

(17 citation statements)

References 33 publications

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“…[9a] We speculated that the polarized carbon-carbon double bonds in electrondeficient olefins might be an equally reactive substitute for carbonyl compounds in C (D,F igure 2). [11] It should be noted that no desired 1,4-adduct was produced in the absence of the ruthenium(II) precatalyst, [12] and as ignificantly lower yield was obtained without the participation of either phosphine ligands or cesium fluoride (40 %a nd 65 %y ield as measured by 1 HNMR, respectively). c) Carbonyl compounds were discovered to act as latent alkyl carbanions via hydrazone formation for conjugateadditions catalyzed by ruthenium with phosphine ligand (this work).…”

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confidence: 99%

Carbonyls as Latent Alkyl Carbanions for Conjugate Additions

Dai

Wang

2017

Angew Chem Int Ed

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Conjugate addition of carbon nucleophiles to electron-deficient olefins is one of the most powerful methods for forming carbon-carbon bonds. Despite great achievements in controlling the selectivity, variation of the carbon nucleophiles remains largely underexplored, with this approach relying mostly on organometallic reagents. Herein, we report that naturally abundant carbonyls can act as latent carbon nucleophiles for conjugate additions through a ruthenium-catalyzed process, with water and nitrogen as innocuous byproducts. The key to our success is homogeneous ruthenium(II) catalysis, combined with phosphines as spectator ligands and hydrazine as the reducing agent. This chemistry allows the incorporation of highly functionalized alkyl fragments into a vast array of electron-deficient olefins under mild reaction conditions in a reaction complementary to the classical organometallic-reagent-based conjugate additions mediated or catalyzed by "soft" transition metals.

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confidence: 99%

Carbonyls as Latent Alkyl Carbanions for Conjugate Additions

Dai

Wang

2017

Angew Chem Int Ed

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“…The presence of substituents (Me, Br and F) on 5-position of the pyrimidine nucleobases had no significant effect on the reaction results (Table 5, entries 7-9). When adenine was used in the Michael reaction, exclusively N9-alkylated products were produced (Table 5, entries [10][11][12][13][14]. However, Michael reactions of 6-chloropurine and hypoxanthine gave N7-isomers beside N9-ones in low yields (Table 5, entries 15 and 16).…”

Section: Resultsmentioning

confidence: 99%

Ionic liquid-accelerated Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters: a rapid approach to carboacyclic nucleosides synthesis

Hasaninejad¹,

Safinejad²,

Zare³

et al. 2008

Arkivoc

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“…[19][20][21][22][23] AzaMichael addition of phthalimide and sulfonamides to α,β-unsaturated esters provides a direct and appealing route toward synthesis of N-alkyl derivatives of these compounds. [24][25][26][27] For N-alkyl phthalimides some biological activities, such as antipsychotic, 28 anti-inflammatory, 29,30 hypolipidemic, 31 and receptor properties have been reported. 32 Furthermore, these compounds are very useful intermediate in organic synthesis as they can be easily converted to primary amines (Gabriel synthesis).…”

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confidence: 99%