Electrochemical Allylation Reactions of Simple Imines in Aqueous Solution Mediated by Nanoscale Zinc Architectures

Huang, Jing‐Mei; Xu-xiao, Wang; Dong, Yunhui

doi:10.1002/ange.201004852

Cited by 12 publications

(2 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…698 Analogously, Huang and co-workers developed an efficient electrosynthesis of homoallylic amines from imines and allyl halides (Figure 42G). 699 The reaction takes place readily in aqueous solutions, using zinc electrodes under galvanostatic conditions. Benzyl and alkyl halides could also be reduced using this protocol, allowing the benzylation/alkylation of imines.…”

Section: Reduction Of Alkyl Halidesmentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

View full text Add to dashboard Cite

show abstract

Section: Reduction Of Alkyl Halidesmentioning

confidence: 99%

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

2017

View full text Add to dashboard Cite

show abstract

“…3d Upon absorption of a photon with minimum energy 2.8 eV, the first excited state of the Pd(0) photocatalyst 5, which, for our reaction mixture is putatively Pd(0)(Xantphos) 2 , donates an electron to iodocyclohexane 1 (E 0 = −0.85 V vs SCE) to form intermediate 6. 14 6 then either (i) undergoes radical addition to styrene 2 to form intermediate 8, which forms 9 and the Heck product 3 following β-hydride elimination, or (ii) rapidly decays to the "oxidative addition product" 7, which undergoes β-hydride elimination to form 9 and the cyclohexene byproduct 4. Following either pathway, the starting Pd(0) catalyst is regenerated from 9 in the presence of base (here, Cs 2 CO 3 ).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Energy Transfer from CdS QDs to a Photogenerated Pd Complex Enhances the Rate and Selectivity of a Pd-Photocatalyzed Heck Reaction

2019

View full text Add to dashboard Cite

This Article describes the design of a colloidal quantum dot (QD) photosensitizer for the Pd-photocatalyzed Heck coupling of styrene and iodocyclohexane to form 2-cyclohexylstyrene. In the presence of 0.05 mol % CdS QDs, which have an emission spectrum that overlaps the absorption spectrum of a key Pd(II)alkyl iodide intermediate, the reaction proceeds with 82% yield for the Heck product at 0.5 mol % loading of Pd catalyst; no product forms at this loading without a sensitizer. A radical trapping experiment and steady-state and transient optical spectroscopies indicate that the QDs transfer energy to a Pd(II)alkyl iodide intermediate, pushing the reaction toward a Pd(I) alkyl radical species that leads to the Heck coupled product, and suppressing undesired β-hydride elimination directly from the Pd(II)alkyl iodide. Functionalization of the surfaces of the QDs with isonicotinic acid increases the rate constant of this reaction by a factor of 2.4 by colocalizing the QD and the Pd-complex. The modularity and tunability of the QD core and surface make it a convenient and effective chromophore for this alternative mode of cooperative photocatalysis.

show abstract

Decarboxylative Coupling of α‐Keto Acids with ortho‐Phenylenediamines Promoted by an Electrochemical Method in Aqueous Media

Wang

Huang

2016

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Electrochemical Allylation Reactions of Simple Imines in Aqueous Solution Mediated by Nanoscale Zinc Architectures

Cited by 12 publications

References 51 publications

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Energy Transfer from CdS QDs to a Photogenerated Pd Complex Enhances the Rate and Selectivity of a Pd-Photocatalyzed Heck Reaction

Decarboxylative Coupling of α‐Keto Acids with ortho‐Phenylenediamines Promoted by an Electrochemical Method in Aqueous Media

Contact Info

Product

Resources

About