HMPA-Catalyzed One-Pot Multistep Hydrogenation Method for the Synthesis of 1,2,3-Trisubstituted Indolines

Zhu, R. S.; Liang, Qian; Gong, Yansheng; Pu, Qingyin; Wang, Z. Y.; Wang, Chuan; Zhou, Li; Sun, Jian

doi:10.1055/s-0036-1590953

Synlett

2017

DOI: 10.1055/s-0036-1590953

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HMPA-Catalyzed One-Pot Multistep Hydrogenation Method for the Synthesis of 1,2,3-Trisubstituted Indolines

R. S. Zhu

Qian Liang

Yansheng Gong

et al.

Abstract: A convenient and facile method was developed for the synthesis of 1,2,3-trisubstituted indolines. Starting from indole derivatives and ketones/aldehydes, the corresponding indoline products could be obtained with high yield by the hexamethylphosphoramide (HMPA) catalyzed indole Friedel–Crafts reaction, reduction and direct reductive amination process.

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Cited by 3 publications

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“…Recently, HMPA and TMEDA have been shown to be suitable activators of highly reactive trichlorosilane in the reductive amination involving aldehydes and ketones with secondary amines. 30,31 Secondary and tertiary amines are achievable through hydrosilylation of C=N bonds using hypervalent hydrosilatrane. 32…”

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confidence: 99%

Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

2019

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A new metal-free reductive amination protocol using a pinacol-derived chlorohydrosilane/pyridine system for the preparation of aminoalkylphenols is described. This method is selective toward iminiums derived from alkylphenol ketones under an in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by computational studies. This method demonstrated high functional group tolerance affording an array of novel aminoalkylphenols in moderate to high yields with equimolar amounts of reactants and a wide substrate scope.

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confidence: 99%

Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

2019

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Recent Advances of Three‐component Reactions of Simple Indoles

et al. 2022

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Indoles are extremely important and versatile building blocks in the field of chemistry. This review highlights the advance made in the three-component reactions of indoles between 2011-2021. The reaction types are classified into three categories based on the trigger mechanisms.Reactions with alkenes, alkynes, aldehydes, imines, ketones, S, Se, etc are discussed. In order to highlight the mechanisms involved, this review has provided specific analysis inside a gray box in each scheme. We hope these studies will promote future research in the indole area.

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Recyclable Polyisobutylene‐Bound HMPA as an Organocatalyst in Recyclable Poly(α‐olefin) Solvents

Bergbreiter

2020

ChemCatChem

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This work describes the synthesis of a PIB-bound hexamethylphosphoramide (HMPA) analog and its applications as a recyclable catalyst in allylation of aldehydes and reduction of enones in a recyclable poly(α-olefin) (PAO) polymeric solvent. Kinetic studies of the allylation reaction show that this PIBbound HMPA analog is as active as HMPA in dichloromethane and PAO and that this PIB-bound catalyst is comparably reactive in heptane and in a PAO solvent. The PIB-bound HMPA catalyst has high phase selective solubility in PAO versus a polar solvent. By using this catalyst in a nonvolatile separable PAO solvent, this catalyst recyclability can be coupled to solvent recyclability, something that is less feasible in a conventional heptane solvent. The result is good recycling of catalyst and solvent through at least 5 cycles using simple gravity-based liquid/ liquid extractions. This is in contrast to HMPA or conventional solvents which are less recyclable.

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HMPA-Catalyzed One-Pot Multistep Hydrogenation Method for the Synthesis of 1,2,3-Trisubstituted Indolines

Cited by 3 publications

References 22 publications

Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

Recent Advances of Three‐component Reactions of Simple Indoles

Recyclable Polyisobutylene‐Bound HMPA as an Organocatalyst in Recyclable Poly(α‐olefin) Solvents

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