Glaser oxidative coupling in ionic liquids: an improved synthesis of conjugated 1,3-diynes

Yadav, J. S.; Reddy, B. V. Subba; Reddy, K. Bhaskar; Gayathri, Kamakolanu Uma; Prasad, A. R.

doi:10.1016/s0040-4039(03)01565-x

Cited by 87 publications

(31 citation statements)

References 25 publications

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“…121 And, ionic liquids have been employed with the classical Hay catalyst (CuCl, TMEDA, O 2 , rt). 122 These solvents have the advantage of being easily recyclable after extraction of the product with an organic solvent.…”

Section: Reactions Of Hydrocarbonsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Reactions Of Hydrocarbonsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…[113][114][115] The homocoupling of terminal alkynes was pioneered by Glaser in 1869, 116,117 and copper salt mediated Glaser coupling and related modified methods are still widely applied in the synthesis of conjugated diynes. [118][119][120][121][122][123][124] In the last decade, palladiumcatalyzed oxidative homocouplings of alkynes with a stoichiometric amount of an oxidant, such as O 2 , 125-127 ahalocarbonyl compounds, 37 and others, [128][129][130][131] have emerged as efficient reactions. Currently, the major methods for constructing unsymmetrical conjugated diynes are the Cadiot-Chodkiewicz coupling and modifications of this reaction, 132,133 i.e.…”

Section: Oxidative Coupling Reactions Of Two Different Terminal Alkynesmentioning

confidence: 99%

Transition-Metal-Catalyzed Oxidative Cross-Coupling Reactions

Liu¹,

Jin²,

Lei³

2010

Synlett

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“…These and related ionic liquids have been successfully applied to hydrogenations [17], alkene dimerizations [18], FriedeleCrafts reactions [19,20], Dielse Alder reactions [21], Heck reactions [22,23], Bechmann condensations [24], Suzuki reactions [25e27], BayliseHillman reactions [28,29], Stille reactions [30,31], and Sonogashira reactions [32]. However, copper-catalyzed cross-coupling reactions in ionic liquids have received less attention [33,34]. The emerging importance of the imidazolium-based ionic liquids in organic synthesis, motivated us to test the efficacy of ionic liquids for CeS coupling reaction.…”

Section: Introductionmentioning

confidence: 99%