B2pin2-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O2 as Oxygen Source and Sole Oxidant

Huang, Jiuzhong; Ouyang, Lu; Li, Jianxiao; Zheng, Jia; Yan, Wuxin; Wu, Wanqing; Jiang, Huanfeng

doi:10.1021/acs.orglett.8b01806

Cited by 17 publications

(8 citation statements)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another important feature of terpyridine ligand is its ability to assist single electron processes, allowing metal-promoted radical processes in catalytic processes. This reactivity was observed with tpy-Cu [62][63][64] and tpy-Pd [65][66][67][68] complexes. Similarly, the nature of Pincer complexes containing electron-deficient ligands will exhibit interesting metal-hydride M-H reactivity.…”

Section: Introductionmentioning

confidence: 65%

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Wei

Shi

et al. 2019

Coordination Chemistry Reviews

195

121

View full text Add to dashboard Cite

As an NNN-tridentate ligand, the 2,2':6',2"-terpyridine plays an important role in coordination chemistry. With three coordination sites and low LUMO, terpyridine and its derivatives are one of the typical Pincer ligand and/or non-innocent ligands in transition metal catalysis. Interesting catalytic reactivities have been obtained with these tpy-metal complexes targeting some challenging transformations, such as CC bond formation and hydrofunctionalization. On the other hand, terpyridine ligands can form "closed-shell" octahedral complexes, which provide a linear and stable linkage in supramolecular chemistry. Numerous supramolecular architectures have been achieved using modified terpyridine ligands including Sierpiński triangles, hexagonal gasket and supramolecular rosettes. This review presents a summary of recent progress regarding transition metal-terpyridine complexes with the focus on their applications in catalysis and supramolecular structure construction. Facile synthesis of terpyridine derivatives is also described. We hope this article can serve to provide some general perspectives of the terpyridine ligand and their applications in coordination chemistry.

show abstract

Section: Introductionmentioning

confidence: 65%

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Wei

Shi

et al. 2019

Coordination Chemistry Reviews

195

121

View full text Add to dashboard Cite

show abstract

“…Jiang et al . reported on the Pd(II)‐catalyzed diacetoxylation of aryl alkenes with O 2 , as the exclusive source of oxygen . The catalyst was assembled in situ from tpy and Pd(OAc) 2 .…”

Section: Terpyridine Complexes As Catalysts For Organic Reactionsmentioning

confidence: 99%

Metal‐Terpyridine Complexes in Catalytic Application – A Spotlight on the Last Decade

Winter

Schubert

2020

ChemCatChem

View full text Add to dashboard Cite

2,2′:6′,2′′‐Terpyridine (tpy) and its derivatives represent highly versatile ligands for the complexation of transition metal ions. Today, such complexes are employed in a highly diverse fashion – including inter alia materials science, opto‐electronics, pharmacy or catalysis. Concerning the latter one, a vast development has led to new or improved applications in both “conventional” organic chemistry (i. e., catalysis of functional‐group interconversions, CH‐activation or cross‐coupling reactions) as well as energy‐related applications (e. g., CO2 reduction, artificial photosynthesis, dye degradation). In this respect, not only homogeneous catalysts (i. e., molecular complexes) but also heterogeneous and recyclable ones have moved to the focus of interest. These heterogeneous structures include 1D metallopolymers, metal‐organic frameworks (MOFs), organic‐inorganic hybrids and bio‐inspired catalysts. We gave a first overview on this topic already in 2011; in here, the methods and implementations established within the last decade as well as relevant contributions from earlier works are presented and discussed.

show abstract

“…Recently, we developed a novel palladium‐catalyzed diacetoxylation of alkenes with great functional group tolerance and excellent yields (Scheme ), which provided a potential approach for the late‐stage modification of natural products . O 2 acted not only as the sole oxidant, but also as an oxygen source.…”

Section: O2 As the Sole Oxidantmentioning

confidence: 99%

“… Selected examples for the diacetoxylation of alkenes . B 2 pin 2 =bis(pinacolato)diboron, terpy=2,2′;6′,2“‐terpyridine.…”

Section: O2 As the Sole Oxidantmentioning

confidence: 99%

“…ChemSusChem 2019ChemSusChem , 12,2911ChemSusChem -2935 www.chemsuschem.org 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim and excellent yields (Scheme 24), which provided ap otential approachf or the late-stage modification of natural products. [39] O 2 acted not only as the sole oxidant, but also as an oxygen source.…”

Section: Atmospheric O 2 As the Sole Oxidantmentioning

confidence: 99%

See 1 more Smart Citation

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Jiang

2019

ChemSusChem

Self Cite

View full text Add to dashboard Cite

Transition‐metal‐catalyzed oxidative functionalization of alkenes has emerged as a powerful and valuable tool in modern organic synthesis. Recently, many methods have been established for the assembly of C−C and C–heteroatom bonds, which provides tremendous possibility for application in biology, medicine, and materials science. However, the use of stoichiometric amounts of strong oxidants leads to poor selectivity, low atom economy, and a series of undesired waste products. By contrast, green oxidants, such as O2, H2O2, or tert‐butyl hydroperoxide (TBHP), have bright prospects due to their attributes of mild, low cost, and great sustainability in transition‐metal‐catalyzed oxidation reactions. Based on the great and unique potential for the development of aerobic reactions, this review mainly highlights homogenous palladium‐catalyzed green oxidations of alkenes that have been reported in recent years. These methods provide new strategies for the transformation and functionalization of alkenes; some of them have also been successfully applied to the synthesis of the core structures of drugs and natural products. Additionally, through in‐depth studies of the reaction mechanisms in this field, it is believed that palladium‐catalyzed green oxidation reactions of alkenes with O2, H2O2, or TBHP will create added value for organic synthetic chemistry.

show abstract

B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant

Cited by 17 publications

References 66 publications

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Terpyridine-metal complexes: Applications in catalysis and supramolecular chemistry

Metal‐Terpyridine Complexes in Catalytic Application – A Spotlight on the Last Decade

Palladium‐Catalyzed Oxidation Reactions of Alkenes with Green Oxidants

Contact Info

Product

Resources

About