Diaminocyclopentadienone Ruthenium Complex Catalyzed Alkylation of Indoles and Ketones with Primary Alcohols DOI Creative Commons

Steffen Skowaisa,

Edgar Haak

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Сен. 9, 2023

Abstract A diaminocyclopentadienone ruthenium complex has proven to be a highly effective catalyst for the alkylation of indoles or ketones with poorly reactive alcohols. The is readily available, air and moisture stable exhibits wide functional group tolerance. environmentally benign procedure follows borrowing hydrogen mechanism requires no excess either component. Various are selectively monoalkylated in high yield.

Язык: Английский

Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles DOI
Subhasree Pal, Amit Kumar Guin, Subhajit Chakraborty

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(10)

Опубликована: Фев. 7, 2024

Abstract Herein we report a sustainable approach for the alkylation of ketones, 9 H ‐fluorene, oxindole, and indole using alcohols as alkylating agent catalyzed by well‐defined air‐stable zinc catalyst ( 1 ) tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline L ). 2–3 mol % efficiently produces substituted α‐alkylated 9‐alkylated fluorenes, C3 ‐alkylated oxindoles, indoles in moderate to good isolated yields. In aerial condition, formation bis(indolyl)methane (BIMs) derivatives were observed when subjected primary alcohols. A few drug molecules containing BIMs prepared The exhibited chemoselectivity during functionalization fluorene with oleyl alcohol β‐citronellol. control experiments, including deuterium labeling performed unveil reaction mechanism indicate that one‐electron reduced azo‐anion radical species [ ]‐formed situ, acts active catalyst. All events occur at redox‐active aryl‐azo which reservoir hydrogen electrons throughout catalytic cycle, keeping Zn(II)‐center template.

Язык: Английский

Процитировано

9
Oxygen Dependent Switchable Selectivity during Ruthenium Catalyzed Selective Synthesis of C3-Alkylated Indoles and Bis(indolyl)methanes DOI
Amit Kumar Guin, Subhasree Pal, Subhajit Chakraborty

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 16755 - 16772

Опубликована: Ноя. 28, 2023

Herein, we report a ligand-centered redox-controlled oxygen-dependent switchable selectivity during ruthenium-catalyzed selective synthesis of C3-alkylated indoles and bis(indolyl)methanes (BIMs). A wide variety BIMs were prepared selectively in moderate to good isolated yields by coupling alcohols, catalyzed well-defined, air-stable, easy-to-prepare Ru(II)-catalyst (1a) bearing redox-active tridentate pincer (L1a). Catalyst 1a efficiently the C3-alkylation under an argon atmosphere while, oxygen environment, exclusively producing BIMs. few drug molecules containing also synthesized efficiently. exhibited excellent chemoselectivity with alcohols internal carbon–carbon double bonds. Mechanistic investigation revealed that coordinated azo-aromatic ligand actively participates catalysis. During dehydrogenation azo-moiety stores hydrogen removed from subsequently transfers alkylideneindolenine intermediate, forming indoles. While transfer scaffold molecular generates H2O2, leaving no scope for hydrogenation rather than it undergoing 1,4-Michael-type addition

Язык: Английский

Процитировано

8
InCl3/TfOH-Mediated Convenient Synthesis of 3-Alkylideneoxindoles from 2-Oxindoles with 1,3-Diones, Ketones, or Aldehydes DOI
Xia Chen, Xiaoyu Zhou, Hailong Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4979 - 4989

Опубликована: Март 27, 2024

Two efficient and convenient methods for the synthesis of 3-alkylideneoxindoles are described in this paper. The InCl3/TfOH-mediated tandem Knoevenagel condensation–deacylation sequence various 2-oxindoles with 1,3-diones or acetoacetate furnished satisfactory to excellent yields (up >99% yield). Employing reaction system, condensation ketones aldehydes also proceeded smoothly produce 3-alkylideneoxindoles. This protocol can be amenable scale up. effect acids on intermolecular competition experiments were investigated understand aspect reaction.

Язык: Английский

Процитировано

1
Fe(II)-Catalyzed Metal-Ligand Cooperative Approach for Selective C3-Alkylation of Indoles DOI

Sutanuva Mandal,

Nanda D. Paul, Subhajit Chakraborty

и другие.

Synlett, Год журнала: 2024, Номер 35(20), С. 2508 - 2514

Опубликована: Авг. 12, 2024

Abstract Herein, we report a straightforward approach for synthesizing C3-alkylated indoles selectively via an iron-catalyzed alkylation of using alcohols as the alkylating agents. A well-defined, air-stable, and easy-to-prepare Fe(II) catalyst redox-active tridentate arylazo scaffold was used catalyst. Various were prepared in moderate to good isolated yields by coupling with different substituted alcohols. The methodology is compatible gram-scale synthesis. Control experiments performed unveil mechanism, which revealed that reaction proceeds borrowing-hydrogen pathway where coordinated azo-aromatic ligand actively participates during catalysis, acting electron hydrogen reservoir.

Язык: Английский

Процитировано

1
New ruthenium(II) isocyanide catalysts for the transfer hydrogenation of ethyl levulinate to γ-valerolactone in C2-C6 alcohols DOI Creative Commons
Lorenzo Biancalana, Nicola Di Fidio, Domenico Licursi

и другие.

Journal of Catalysis, Год журнала: 2024, Номер unknown, С. 115761 - 115761

Опубликована: Сен. 1, 2024

Язык: Английский

Процитировано

1
Base-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones DOI Creative Commons
Xia Chen, Xiaoyu Zhou, Ming Bao

и другие.

Molecules, Год журнала: 2023, Номер 28(21), С. 7450 - 7450

Опубликована: Ноя. 6, 2023

The N-functionalized indole is a privileged structural framework in wide range of bioactive molecules. nucleophilic addition between indoles with vinylene carbonate proceeded smoothly the presence K2CO3 as catalyst to produce novel indolyl-containing skeletons and 4-indolyl-1,3-dioxolanones satisfactory excellent yields (up >97% yield). Various synthetically useful functional groups, such halogen atoms, cyano, nitro, methoxycarbonyl remained intact during regioselective N-H reactions. developed catalytic system also could accommodate 2-naphthalenol achieve target O-H additive product good yield.

Язык: Английский

Процитировано

2
Reduction of C=X to CH2 DOI
Pauline Adler

Elsevier eBooks, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

0
C3-Alkylation of Indoles via Ru-Catalyzed Transfer Hydrogenation and Borrowing Hydrogen Approaches DOI
Mark Lautens, Jonathan Bajohr

Synfacts, Год журнала: 2023, Номер 19(03), С. 0253 - 0253

Опубликована: Фев. 13, 2023

Key words ruthenium catalysis - transfer hydrogenation borrowing hydrogen

Язык: Английский

Процитировано

0
Diaminocyclopentadienone Ruthenium Complex Catalyzed Alkylation of Indoles and Ketones with Primary Alcohols DOI Creative Commons

Steffen Skowaisa,

Edgar Haak

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Сен. 9, 2023

Abstract A diaminocyclopentadienone ruthenium complex has proven to be a highly effective catalyst for the alkylation of indoles or ketones with poorly reactive alcohols. The is readily available, air and moisture stable exhibits wide functional group tolerance. environmentally benign procedure follows borrowing hydrogen mechanism requires no excess either component. Various are selectively monoalkylated in high yield.

Язык: Английский

Процитировано

0