An Efficient Route to 3‐Amidylindoles <i>via</i> a Palladium‐ Catalyzed Tandem Reaction of 2‐Alkynylanilines with Isocyanides

Qiu, Guanyinsheng; Chen, Chen; Yao, Liangqing; Wu, Jie

doi:10.1002/adsc.201300198

Cited by 61 publications

(21 citation statements)

References 45 publications

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“…Alternatively, Yao, Wu, and co-workers employed a tandem protocol to develop synthetic methods for the preparation of similar indole-3-carboxamides by use of 2-alkynylanilines. 27 Accordingly, the combination of N,N-dimethyl-2-alkynylanilines, isocyanides, and AgOAc as oxidant in the presence of Pd(II) catalyst gives indole-3-carboxamides in good to high yields. Replacing AgOAc with other oxidants led to inferior yields.…”

Section: Special Topic Synthesis Scheme 4 Amidation Of Indoles By Isomentioning

confidence: 99%

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

et al. 2020

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The synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic molecules and pharmaceutical candidates. This review gives an overview of the achievements in isocyanide-based transition metal and inner transition metal catalyzed amide formation and discusses highlights of the proposed distinct mechanisms.1 Introduction2 Synthesis of Arenecarboxamides3 Synthesis of Alkanamides4 Synthesis of Cyclic Amides5 Formation of Alkynamides6 Formation of Acrylamide-like Molecules7 Formation of Ureas and Carbamates8 Conclusion

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Section: Special Topic Synthesis Scheme 4 Amidation Of Indoles By Isomentioning

confidence: 99%

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

et al. 2020

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“…Wu and co-workers reported the synthesis of indolecarboxamides 289 from N,N-dimethyl-2-alkynylanilines 288 (Scheme 87). [130] Ther eactioni sp roposed to be initiated by a5 -endo-dig aminopalladation fol- lowed by isocyanide insertion. Reductive elimination of the imidoyl-Pd(II)OAc complex forms O-acetyl imidate 290 which rearranges to form the amidate.…”

Section: P-system Activation/isocyanide Insertionmentioning

confidence: 99%

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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“…(49)]. [85] Primary, secondary, and tertiary aliphatic isonitriles react well but 2,6-dimethylphenyl isocyanide failed to react. All of the successful substrates contained an aromatic or aliphatic substituent R 3 on the alkyne.…”

Section: Condensations Leading To Pyrroles and Indolesmentioning

confidence: 99%

“…Palladium acetate catalyzes the condensation of isonitriles 163 with 2‐alkynylanilines 214 to afford 3‐amidylindoles 215 [Eq. (49)] 85 Primary, secondary, and tertiary aliphatic isonitriles react well but 2,6‐dimethylphenyl isocyanide failed to react.…”

Section: Condensations Leading To Pyrroles and Indolesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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An Efficient Route to 3‐Amidylindoles via a Palladium‐ Catalyzed Tandem Reaction of 2‐Alkynylanilines with Isocyanides

Abstract: A palladium-catalyzed reaction of 2-alkyn-A C H T U N G T R E N N U N G ylaniline, isocyanides, and silver acetate is described, leading to 3-amidylindoles in moderate to good yields. During the process, five new bonds are formed with high reaction efficiency in one-pot procedure.

Cited by 61 publications

References 45 publications

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry

Advances in Palladium‐Catalyzed Cascade Cyclizations

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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