Pd-Catalyzed Indole Synthesis via C–H Activation and Bisamination Sequence with Diaziridinone

Wang, Jianjun; Xiao-feng, Sun; Hu, Daguo; Shi, Yian

doi:10.1021/acs.orglett.1c02757

Cited by 10 publications

(7 citation statements)

References 68 publications

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“… , Consequently, numerous synthetic methods have been developed to access the 2-arylindole substructure. Classic routes include the Fischer indole synthesis while contemporary approaches employ transition-metal catalysts, including direct C-2 arylation of pre-existing indoles, − and intramolecular cyclization of functionalized anilines, − and many others. − Some of these approaches employ harsh reagents, highly functionalized precursors, or cryogenic temperatures that are challenging to access on scale. Therefore, more straightforward, efficient, and practical synthetic methods without addition of transition metals for the assembly of 2-arylindoles remain in demand.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Indoles via Domino Reactions of 2-Methoxytoluene and Nitriles

et al. 2022

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2-Arylindoles are privileged structures widely present in biologically active molecules. New sustainable synthetic routes toward their synthesis are, therefore, in high demand. Herein, a mixed base-promoted benzylic C−H deprotonation of commercially available ortho-anisoles, addition of the resulting anion to benzonitriles, and S N Ar to displace the methoxy group provide indoles. A diverse array of 2-arylindoles is prepared with good yields (>30 examples, yields up to 99%) without added transition metal catalysts.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Indoles via Domino Reactions of 2-Methoxytoluene and Nitriles

et al. 2022

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“…Our group recently reported the synthesis of heteroatomrich spirocycles via a domino Mizoroki−Heck/C−H activation strategy of compounds with preinstalled heterocycles. 3b Advancing our research program in heterocycle synthesis, herein we report a domino Narasaka−Heck/C−H activation/ amination reaction using diaziridinone, 6 generating novel nitrogen-rich bis-heterocyclic spirocycles (Scheme 1C).…”

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confidence: 99%

Pd-Catalyzed Domino Narasaka–Heck/C–H Activation/Amination Reactions: Synthesis of Bis-heterocyclic Spirocycles

et al. 2023

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The palladium-catalyzed synthesis of bis-heterocyclic spirocycles containing both pyrroline and indoline motifs is reported. Di-tert-butyldiaziridinone is used to functionalize palladacycles generated in situ via domino Narasaka−Heck/C−H activation reactions. The reaction is readily scalable, and the spirocyclic products can undergo deprotection, reduction, and (3 + 2) cycloadditions, highlighting their synthetic utility. Additionally, kinetic isotope effect experiments support a turnover-limiting C−H functionalization step in the catalytic cycle.

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“…Recently, we have found that di-t-butyldiaziridinone (5) can also intercept a pallada(II)heterocycle intermediate to give the ortho-aryl C-H amination product with an N-(quinolin-8-yl) benzamide substrate. 12,13 Now we report that the vinyl C-H amination process is feasible for N-(quinolin-8-yl)acrylamides, providing a variety of 3-amino-N-(quinolin-8-yl)acrylamides (Scheme 2). While the metal-catalyzed aryl C-H amination has been extensively studied, the corresponding direct vinyl C-H amination for the formation of acyclic enamines or their derivatives is surprisingly rare.…”

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confidence: 99%