- Copper-catalyzed oxyvinylation of diazo compounds
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A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.
- Pisella, Guillaume,Gagnebin, Alec,Waser, Jerome
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- Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds
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Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one-step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.
- Hari, Durga Prasad,Schouwey, Lionel,Barber, Verity,Scopelliti, Rosario,Fadaei-Tirani, Farzaneh,Waser, Jerome
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- Low-Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands
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The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one-pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) an
- Hari, Durga Prasad,Pisella, Guillaume,Wodrich, Matthew D.,Tsymbal, Artem V.,Tirani, Farzaneh Fadaei,Scopelliti, Rosario,Waser, Jerome
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supporting information
p. 5475 - 5481
(2021/01/21)
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- Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers
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Multicomponent reactions provide efficient means to access molecular complexity. Herein, we report a copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers. Extensive variations of the three partners of the reaction is possible, leading to highly functionalized and structurally diverse products under mild conditions. Alkynylation of a copper ylide intermediate is postulated as key step for this transformation.
- Pisella, Guillaume,Gagnebin, Alec,Waser, Jér?me
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supporting information
p. 10199 - 10204
(2020/07/17)
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- Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds
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Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usi
- Hari, Durga Prasad,Waser, Jerome
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p. 8420 - 8423
(2017/07/06)
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- Exceptionally high trans (anti) stereoselectivity in catalytic cyclopropanation reactions
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Exceptionally high trans (anti) stereoselectivities are obtained in rhodium(II) carboxylate and carboxamide catalyzed alkene cyclopropanation reactions with 2,6-di-tert-butyl-4-methylphenyl diazoacetate (BDA). With monosubstituted ethylenes, use of rhodiu
- Doyle, Michael P.,Bagheri, Vahid,Wandless, Thomas J.,Harn, Nancy K.,Brinker, David A.,Eagle, Cassandra T.,Loh, Kuo-Liang
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p. 1906 - 1912
(2007/10/02)
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