Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis

Nomiyama, Shota; Hondo, Takehiro; Tsuchimoto, Teruhisa

doi:10.1002/adsc.201500502

Cited by 28 publications

(21 citation statements)

References 95 publications

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“…The indole moiety is a prominent structural motif in significant organic molecules including alkaloids, pharmaceuticals, and functional materials . In this context, we decided to evaluate the incorporation of indole to our carbohydrate systems, 14 and 15 .…”

Section: Resultsmentioning

confidence: 99%

Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

2018

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Novel pyranose derivatives that display Ferrier‐ and Ferrier‐Nicholas‐like reactivity have been designed. These systems: 1‐C‐alkynyl‐2‐deoxy‐2‐C‐methylene pyranosides (Ferrier), and their corresponding dicobalthexacarbonyl alkenyl derivatives (Ferrier‐Nicholas), which can be accessed by a concise synthetic route from commercially available tri‐O‐acetyl‐d‐glucal, allow the incorporation of two nucleophiles (at positions C‐3 and C‐2′) in the pyranose ring. The study of these systems has resulted in the discovery of novel reaction patterns that allow, among others, access to open‐chain derivatives, branched pyranosides, 1,6‐anhydro derivatives and, when reacting with indole, access to a new family of tetracyclic indole‐containing carbohydrate derivatives, namely, cyclohepta[b]indole‐fused glycals. The latter are, most likely, formed by a bis Ferrier‐type rearrangement followed by an unusual intramolecular 7‐endo‐dig Friedel–Crafts alkenylation of one of the indole moieties by the C‐1 alkyne.

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Section: Resultsmentioning

confidence: 99%

Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

2018

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“…To keep this Review a reasonable length, only reactions involving new σ‐bond formations at the carbonyl and carboxylic carbon directly or through minimal derivation will be included. Exhaustive reduction (e.g., carbonyl to methylene, carboxyl to methyl), partial deoxygenation [1–5] and reactions that rely on simple condensation (e.g., carbonyl reductive amination, aldol‐type reaction [6] ) or those necessitating multistep manipulation [7] are beyond our scope and will not be discussed in detail unless closely related.…”

Section: Introductionmentioning

confidence: 99%

Deoxygenative Functionalizations of Aldehydes, Ketones and Carboxylic Acids

Huang

2022

Angewandte Chemie

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The simple and efficient conversion of carbonyl compounds into functionalized alkanes via deoxygenation is highly enabling in chemical synthesis. This Review covers the recent methodology development in carbonyl and carboxyl deoxygenative functionalizations, highlighting some representative and significant contributions in this field. These advances are categorized based on the reactivity patterns of some oxygenated feedstock compounds, including aldehydes, ketones and carboxylic acids. Four types of reactive intermediates arising from aldehydes and ketones during the deoxygenation, namely, bis‐electrophiles, carbenoids, bis‐nucleophiles and alkyl radical equivalents, are presented, while the carboxylic acids mainly behave as tris‐electrophiles when deoxygenated. In each subcategory, selected examples are organized according to the type of bond formation and discussed from a generalized mechanistic perspective.

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“…9 Ketones can be directly used for the preparation of 3-alkylindoles but obviously a silane reducing agent must be present in the reaction mixture. [10][11] Modern procedures for the alkylation of indoles employ primary and secondary alcohols as reactants in metal redox catalyzed processes, [12][13][14] or secondary alcohols in metal-free redox chain reactions. 15 Finally a successful method using primary and secondary amines in a Ru-catalyzed process is available for the synthesis of 3-alkylindoles.…”

Section: Introductionmentioning

confidence: 99%

3-Alkylated indoles by reduction of sulfonyl indoles under flow chemical conditions

Chiurchiù¹,

Palmieri²,

Petrini³

2019

Arkivoc

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Reduction of 3-(1-arylsulfonylalkyl) indoles (sulfonyl indoles) using polymer-supported sodium borohydride under flow chemical conditions allows an efficient synthesis of 3-alkylindoles with a notable waste minimization and reduced solvent consumption. The flow conditions can be also applied to the synthesis of sulfonyl indoles which can be obtained by a three-component coupling of indoles with aldehydes and ptoluenesulfinic acid. Using the two-step flow chemical approach, 3-alkylindoles can be directly obtained from their remote indole and aldehyde precursors.

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Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis

Cited by 28 publications

References 95 publications

Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides

Deoxygenative Functionalizations of Aldehydes, Ketones and Carboxylic Acids

3-Alkylated indoles by reduction of sulfonyl indoles under flow chemical conditions

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