Highly efficient synthesis of flavones via Pd/C-catalyzed cyclocarbonylation of 2-iodophenol with terminal acetylenes

Zhu, Fengxiang; Li, Yahui; Wang, Zechao; Wu, Xiao‐Feng

doi:10.1039/c6cy00613b

Cited by 37 publications

(15 citation statements)

References 32 publications

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“…Wu's group recently reported the Pd/C‐catalyzed ligand‐free cyclocarbonylation of 2‐iodophenol with terminal acetylenes in the presence of Et 2 NH and CO to afford the corresponding flavones in toluene at 110 °C [Eq. (76)] . A variety of flavone derivatives was obtained in excellent yields with excellent functional group tolerance.…”

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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“…The ligand‐free procedure reported by Wu, starting from 2‐iodophenol and terminal acetylenes as the substrates, involved the use of Pd/C as the heterogeneous and recyclable catalyst, CO and Et 2 NH as the base (Scheme ) . The cyclocarbonylation of 2‐iodophenol with heteroaromatic substituted‐, and both electron‐rich and electron‐poor aromatic substituted‐ terminal acetylenes proceeded well, as well as aliphatic acetylenes reacted with 2‐iodophenol, affording the desired chromone derivative 41 in a selective manner and in good to excellent yields (Scheme ) …”

Section: Pd‐catalyzed Carbonylative Synthesis Of O‐heterocyclesmentioning

confidence: 99%

Heterocycle Synthesis through Pd‐Catalyzed Carbonylative Coupling

2019

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Heterocyclic chemistry is one of the most important and attractive areas of organic chemistry. It involves the preparation of compounds endowed with very high structural diversity and plays a central role in a multitude of highly developed areas: fine chemicals, drugs, flavors, dyes, engineered materials, and many other kinds of products contain at least one heterocyclic ring in their molecular structure. Therefore, the discovery of new methods for heterocycle synthesis is a significant objective of modern organic chemists, especially if prepared in environmentally benign and synthetically efficient ways. In this context, this minireview focuses on the synergy of two green strategies, namely multicomponent reactions and palladium‐catalyzed carbonylations, for the construction of a wide variety of heterocyclic systems. These processes are of considerable interest because they combine synthetic efficiency with respect for the environment.

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“…However, most of these protocols have considered high loading of both catalysts and phosphine ligands and also led to low yields of the corresponding chromones when terminal alkyl alkynes reacted with 2-iodophenols in the presence of carbon monoxide. 33 , 35 , 40 − 42 …”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Chromones via Cyclocarbonylative Sonogashira Coupling Catalyzed by Highly Active Bridged-Bis(N-Heterocyclic Carbene)Palladium(II) Complexes

2020

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The one-pot regioselective and catalytic synthesis of bioactive chromones and flavones was achieved via phosphine-free cyclocarbonylative Sonogashira coupling reactions of 2-iodophenols with aryl alkynes, alkyl alkynes, and dialkynes. The reactions are catalyzed by new dibromidobis(NHC)palladium(II) complexes. The new bridged N , N ′-substituted benzimidazolium salts ( L1 , L2 , and L3 ) and their palladium complexes C1 , C2 , and C3 were designed, prepared, and fully characterized using different physical and spectroscopic techniques. The molecular structures of complexes C1 and C3 were determined by single-crystal X-ray diffraction analysis. They showed a distorted square planar geometry, where the Pd(II) ion is bonded to the carbon atoms of two cis NHC carbene ligands and two cis bromido anions. These complexes displayed a high catalytic activity in cyclocarbonylative Sonogashira coupling reactions with low catalyst loadings. The regioselectivity of these reactions was controlled by using diethylamine as the base and DMF as the solvent.

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Highly efficient synthesis of flavones via Pd/C-catalyzed cyclocarbonylation of 2-iodophenol with terminal acetylenes

Cited by 37 publications

References 32 publications

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Heterocycle Synthesis through Pd‐Catalyzed Carbonylative Coupling

Regioselective Synthesis of Chromones via Cyclocarbonylative Sonogashira Coupling Catalyzed by Highly Active Bridged-Bis(N-Heterocyclic Carbene)Palladium(II) Complexes

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