Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

Wu, Yinuo; Choy, Pui Ying; Mao, Fei; Kwong, Fuk Yee

doi:10.1039/c2cc37352a

Cited by 138 publications

(35 citation statements)

References 66 publications

(17 reference statements)

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“…At the end of 2012, three procedures for the acylation of acetanilides with toluenes were developed independently,47 with catalytic systems based on Pd(OAc) 2 /TBHP. Sun’s procedure used DMSO as solvent,47a whereas Kwong and co‐workers used chlorobenzene,47b and Zhang and co‐workers used toluenes both as solvent and reagent 47c. Good yields of ketones were obtained in all cases (Scheme ).…”

Section: Discussionmentioning

confidence: 99%

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

2015

Chemistry A European J

131

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In this Minireview, the major achievements in the acylation of arenes and heteroarenes by C-H activation with aroyl groups are summarized and discussed. As the products are carbonyl-containing compounds that are typical products from carbonylation chemistry, the possible inspirations for these reactions are also discussed, as are mechanistic issues and possible problems for carbonylative diaryl ketone synthesis by C-H activation.

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Section: Discussionmentioning

confidence: 99%

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

2015

Chemistry A European J

131

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“…Different R 3 substitution patternsd id not decrease the yield significantly.I nas imilar approach, Kwong and co-workers reported the synthesis of N-alkyl-2-aminobenzophenones [189] and ortho-acylacetanilides. [190] Ap alladium-catalyzed cascade reactionw as reported during the total syntheseso fd ictyodendrins Ba nd Eb yJ ia et al (Scheme133). [191] Dictyodendrins Ba nd Eh ave interesting telomerase inhibiting activities, which are of potential interest for cancer treatment.…”

Section: C-h Activationmentioning

confidence: 97%

Advances in Palladium‐Catalyzed Cascade Cyclizations

Biemolt

Ruijter

2018

Adv Synth Catal

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Thep ast decades in organic chemistry have witnessed significant improvements in synthetic efficiency as ar esult of considerable progress in cascade reactions,t andem reactions,a nd related onepot processes. These methods are less time-consuming andp roduce less waste comparedt ot he classical stepwise approach. However, cascade chemistry requires am ore careful design and compatible reaction types for success.P alladium-catalyzed cross-coupling reactions,w ith their well understoodm ultistep catalytic cycles,f orm ap romising basis for the design of cascade reactions.F urthermore,t hey are compatible with ar ange of functional groups and can be combined with ar ange of secondary transformations. Ther esulting palladium-catalyzed cascade reactions have provided access to ap lethorao fc omplex small molecules of high medicinal relevance.T his review providesa no verview of the developments in palladium-catalyzed cascade reactions since 2011, classified according to the initiation, propagation, andtermination steps comprising the palladium cascade reactions.T hisc lassification should assist the reader and may provide inspiration for the design of newc ascade reactions.

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“…Kwong et al demonstrated the Pd(II)‐catalyzed tandem cross‐coupling reaction of acetanilide ( 30 ) and 2‐methylbenzoxazole ( 31 ) for the preparation of N ‐(2‐(benzo[ d ]oxazole‐2‐carbonyl)phenyl)acetamide ( 32 ). Under the developed conditions, the toluene can be employed as an effective acyl precursor in the oxidative coupling between two C–H bonds (Scheme ). The present dehydrogenative Pd/TBHP‐catalyzed ortho ‐acylation approach proceeds under mild reaction conditions.…”

Section: Synthesis Of 2‐keto‐annulated Oxazolesmentioning

confidence: 99%

Overview on Recent Approaches towards Synthesis of 2‐Keto‐annulated Oxazole Derivatives

Aljaar

Gujjarappa

Al-Refai

et al. 2019

Journal of Heterocyclic Chem

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In recent years, oxazole derivatives have emerged as one of the formidable groups of compounds in the field of medicinal chemistry and drug discovery. The titled compounds 2‐keto‐annulated oxazoles play an important role towards the medicinal aspects. There has been an appearance of a significant number of research articles and reviews to explore the wide utility of oxazole derivatives. However, till now, there has been no dedicated review published focusing on the synthesis of 2‐keto‐annulated oxazole derivatives. Herein, we have presented the recent protocols available in literature for the synthesis of 2‐keto‐annulated oxazoles and highlighted the advantages of these methods that would attract the attention of a broad range of readers in the chemistry community.

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Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides

Cited by 138 publications

References 66 publications

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

Acylation of (Hetero)Arenes through CH Activation with Aroyl Surrogates

Advances in Palladium‐Catalyzed Cascade Cyclizations

Overview on Recent Approaches towards Synthesis of 2‐Keto‐annulated Oxazole Derivatives

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