Palladium-Catalyzed Direct Cross-Coupling Reaction of Glycals with Activated Alkenes

Bai, Yaguang; Zeng, Jing; Cai, Shuting; Liu, Xuewei

doi:10.1021/ol201734w

Cited by 64 publications

(28 citation statements)

References 42 publications

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“…The first example of this type of reactivity was reported by Liu et al. in 2011 and involved the coupling of glycals with substituted alkenes [60] . The best conditions require the use of catalytic quantities of Pd(OAc) 2 and the presence of Cu(OTf) 2 , in a mixture of solvents (dimethylacetamide (DMA)/AcOH=1:1) under an atmosphere of O 2 (Scheme 25, conditions A).…”

Section: New Emerging Methodsmentioning

confidence: 99%

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Emerging Organometallic Methods for the Synthesis of C‐Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches

Ghouilem

Robichon

Bideau

et al. 2020

Chemistry A European J

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Transition‐metal‐catalyzed C−H functionalization and photoredox nickel dual catalysis have emerged as innovative and powerful avenues for the synthesis of C‐branched glycosides. These two concepts have been recently established and provide efficient and mild methods for accessing a series of valuable complex C‐branched glycosides of great interest. Herein, recent developments in the synthesis of C‐branched aryl/alkenyl/alkyl glycosides through these two approaches are highlighted.

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Section: New Emerging Methodsmentioning

confidence: 99%

“… Pd II ‐catalyzed C2‐vinyl glycosides reported by Liu et al [60] . BQ: p ‐benzoquinone, pc: phthalocyanine.…”

Section: New Emerging Methodsmentioning

confidence: 99%

Emerging Organometallic Methods for the Synthesis of C‐Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches

Ghouilem

Robichon

Bideau

et al. 2020

Chemistry A European J

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“…Recently, Liu and co‐workers reported a palladium‐catalyzed method for the alkenylation of glycals with activated alkenes 5i. This method works very well with glycals, which are fairly stable molecules and activated olefins as coupling partners.…”

Section: Methodsmentioning

confidence: 99%

Selective Hydrodeoxygenation of Cyclic Vicinal Diols to Cyclic Alcohols over Tungsten Oxide–Palladium Catalysts

et al. 2014

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Hydrodeoxygenation of cyclic vicinal diols such as 1,4-anhydroerythritol was conducted over catalysts containing both a noble metal and a group 5-7 transition-metal oxide. The combination of Pd and WOx allowed the removal of one of the two OH groups selectively. 3-Hydroxytetrahydrofuran was obtained from 1,4-anhydroerythritol in 72 and 74% yield over WOx -Pd/C and WOx -Pd/ZrO2 , respectively. The WOx -Pd/ZrO2 catalyst was reusable without significant loss of activity if the catalyst was calcined as a method of regeneration. Characterization of WOx -Pd/C with temperature-programmed reduction, X-ray diffraction, and transmission electron microscopy/energy-dispersive X-ray spectroscopy suggested that Pd metal particles approximately 9 nm in size were formed on amorphous tungsten oxide particles. A reaction mechanism was proposed on the basis of kinetics, reaction results with tungsten oxides under an atmosphere of Ar, and density functional theory calculations. A tetravalent tungsten center (W(IV) ) was formed by reduction of WO3 with the Pd catalyst and H2 , and this center served as the reductant for partial hydrodeoxygenation.

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“…By far the most commonly used substrates for C–H functionalization at C2 are glycals, and most of this chemistry has been developed within the last decade. Liu and co‐workers used palladium‐catalyzed cross‐coupling to couple glycals (e.g., 56 ) with activated alkenes and thereby to achieve easy access to C‐functionalization of C2 without losing the alkene functionality (Scheme ) . The conditions were optimized and it was found that Pd(OAc) 2 (10–20 %) together with Cu(OTf) 2 as the oxidant gave the highest yield at 70 °C with use of DMA/AcOH as the solvent mixture.…”

Section: C–h Functionalization Of C2–h To C6–hmentioning

confidence: 99%

C–H Functionalization on Carbohydrates

2016

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Functionalization of C-H bonds has received significant attention in organic chemistry during the last decade and it is still a "hot" topic. In particular, C-H modification of natural products has benefitted from this development. Carbohydrates are densely functionalized natural products, and methods for their functionalization are therefore very attractable. This review presents methods from the last five decades and gives an over-

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Palladium-Catalyzed Direct Cross-Coupling Reaction of Glycals with Activated Alkenes

Cited by 64 publications

References 42 publications

Emerging Organometallic Methods for the Synthesis of C‐Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches

Emerging Organometallic Methods for the Synthesis of C‐Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches

Selective Hydrodeoxygenation of Cyclic Vicinal Diols to Cyclic Alcohols over Tungsten Oxide–Palladium Catalysts

C–H Functionalization on Carbohydrates

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