Generation of Arylated Quinones by Iron‐Catalyzed Oxidative Arylation of Phenols: Formal Synthesis of Phellodonin, Sarcodonin ε, Leucomelone and Betulinan A

Deb, Arghya; Agasti, Soumitra; Saboo, Tapish

doi:10.1002/adsc.201301084

Cited by 22 publications

(6 citation statements)

References 72 publications

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“…The arylation of phenols with arylboronic acids under oxidative conditions has been reported by Maiti and co-workers to provide arylated quinones in good yields (Scheme ) . Iron(III) sulfate was applied as catalyst for this transformation.…”

Section: Miscellaneousmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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Section: Miscellaneousmentioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…Iron-catalyzed direct arylation of heterocycles and quinones has recently been reported by Komeyama’s group using arylboronic acids . We have also independently reported similar arylation reactions involving heterocycles and quinones . Unfortunately, when our reaction condition was applied to N -methyl-2-pyridone, only 7% arylated pyridone was obtained.…”

Section: Introductionmentioning

confidence: 63%

Iron-Catalyzed Regioselective Direct Arylation at the C-3 Position of N-Alkyl-2-pyridone

Modak

Rana

2014

J. Org. Chem.

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A number of pharmaceutical compounds possess an arylated 2-pyridone moiety. The existing reports using expensive starting materials and/or superstoichiometric metal salts have prompted us to explore a possible user-friendly method for their synthesis. In this report, we demonstrate an easy-to-handle reaction condition with an iron catalyst for the exclusive generation of C-3-arylated pyridone via C-H functionalization.

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“…Next, a more comprehensive investigation of the catalyst and oxidant stoichiometries was conducted. The results were unfavorable when the catalyst loading was either decreased to 5 mol% or increased to 50 mol% (Table 1, entries [12][13][14]. Regarding oxidant loading, both an increase to 7 equiv.…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed One‐Pot Synthesis of 1,3,4‐Oxadiazol‐2(3H)‐ones using DMF as the Carbonyl Source

Jiang,

Su,

Ablajan

et al. 2024

Eur J Org Chem

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A series of 1,3,4‐oxadiazol‐2(3H)‐ones were prepared by an efficient copper‐catalyzed one‐pot reaction of arylhydrazides, arylboronic acids and DMF. Moderate to good yield of 1,3,4‐oxadiazol‐2(3H)‐ones were obtained using DMF as the carbonyl source and arylboronic as the aryl source. This reaction involved ligand exchange and transmetalation of copper catalysts with arylhydrazides and arylboric acids, followed by reductive elimination and intramolecular cyclization. Compared to the previous work, this work employs the stable and readily available aryl hydrazide and arylboronic substrates that enhance the practicality of this strategy, and this strategy features a short reaction time, relatively low heating temperature, convenient and more secure. Further, this protocol has the features of high functional group tolerance and reaction scalability.

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Generation of Arylated Quinones by Iron‐Catalyzed Oxidative Arylation of Phenols: Formal Synthesis of Phellodonin, Sarcodonin ε, Leucomelone and Betulinan A

Abstract: In a few cases NaOH is found advantageous over K2CO3.

Cited by 22 publications

References 72 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Iron-Catalyzed Regioselective Direct Arylation at the C-3 Position of N-Alkyl-2-pyridone

Copper‐Catalyzed One‐Pot Synthesis of 1,3,4‐Oxadiazol‐2(3H)‐ones using DMF as the Carbonyl Source

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