ChemInform Abstract: Pd(0)‐Catalyzed Dearomative Diarylation of Indoles.

Petrone, David A.; Kondo, Masaru; Zeidan, Nicolas; Lautens, Mark

doi:10.1002/chin.201636122

Cited by 2 publications

(2 citation statements)

References 13 publications

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“…The reported procedure was followed. 20 To a solution of compound 3a (19.9 mg, 0.2 mmol, 2.0 equiv) in anhydrous THF (1.5 mL) was added BH 3 •DMS (16.8 mg, 2 equiv) dropwise at 25 °C. The solution was heated to reflux and monitored by TLC until the completion of the reaction.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

Dong

Zhang

et al. 2019

J. Org. Chem.

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An efficient synthesis of N-fused polycyclic and 2,3-disubstituted indoles by copper-catalyzed direct annulation/acyl migration reaction of enaminones is reported. This strategy features cheap and low loading of the catalyst/ligand, readily available starting materials, and good functional group compatibilities. Notably, allyl-containing substrates are also tolerated, which allows the downstream derivatization toward indole alkaloids.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

Dong

Zhang

et al. 2019

J. Org. Chem.

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“…10 In this context, Lautens, Liang, and our group have developed a number of domino dearomative Heck/ anionic capture sequences on the basis of a dearomative Heck reaction. 11,12 Various 2,3-disubstituted indoline derivatives were achieved by the dearomative difunctionalization of indoles, which included Heck/cyanation, 13 Heck/Suzuki, 14 Heck/Sonogashira, 15 and Heck/borylation 16 domino coupling reactions. Nevertheless, the enantiocontrol of such reactions still remains difficult and further development of dearomative difuncntionalization reaction is in high demand.…”

mentioning

confidence: 99%

Palladium-Catalyzed Dearomative Arylvinylation Reaction of Indoles with N-Arylsulfonylhydrazones

Liang

Wang

et al. 2019

Organometallics

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A Pd-catalyzed dearomative arylvinylation reaction of indoles with N-arylsulfonylhydrazones as coupling partners is developed, which proceeds via a domino sequence involving dearomative carbopalladation, Pd-carbene migratory insertion, and regioselective β-hydride elimination. A range of 3-vinylindolines bearing vicinal quaternary and tertiary carbon stereocenters is achieved in moderate yields. The enantioselective reaction was established by using a chiral BINOL-based phosphoramidite ligand, which led to the arylvinylation products in good enantiomeric ratios and excellent diastereoselectivities.

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ChemInform Abstract: Pd(0)‐Catalyzed Dearomative Diarylation of Indoles.

Abstract: A fully syn‐selective Pd(0)‐catalyzed dearomative indole 1,2‐diarylation is presented by using PtBu3 as the ligand.

Cited by 2 publications

References 13 publications

Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles

Palladium-Catalyzed Dearomative Arylvinylation Reaction of Indoles with N-Arylsulfonylhydrazones

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