Zn(II)-Stabilized Azo-Anion Radical-Catalyzed Dehydrogenative Synthesis of Olefins DOI
Subhasree Pal, Amit Kumar Guin,

Subhankar Khanra

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using Zn(II) complex [ZnLCl2] (1) redox-noninnocent ligand 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L), various (E)-olefins were prepared in good yields by coupling with sulfones aryl cyanides under an inert atmosphere. Under aerial atmosphere, vinyl nitriles isolated up to 82% yield reacting benzyl presence 1. Control experiments mechanistic investigation indicate active involvement aryl-azo electron hydrogen reservoir, permitting 1 perform promising catalyst.

Язык: Английский

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds DOI
Sourajit Bera, Lalit Mohan Kabadwal, Debasis Banerjee

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(9), С. 4607 - 4647

Опубликована: Янв. 1, 2024

This review collectively discussed the utilisation of alcohols in various organic transformations and their application toward intermediates drugs, drug derivatives natural product-like molecules.

Язык: Английский

Процитировано

16
Recent advances on cross-coupling of alcohols via borrowing hydrogen catalysis DOI

Suteerna Mullick,

Adrija Ghosh, Debasis Banerjee

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(30), С. 4002 - 4014

Опубликована: Янв. 1, 2024

This article highlights the recent advances and significance of β-alkylation reactions towards synthesis higher order alcohols.

Язык: Английский

Процитировано

14
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

8
CrCl2-catalyzed α-alkylation of carbonyl compounds via a borrowing hydrogen approach DOI

Dongyue Wei,

Baojin Feng,

Qing Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 1955 - 1962

Опубликована: Янв. 1, 2024

A new and efficient catalytic system for sustainable α-alkylation of carbonyl compounds with alcohols via a borrowing hydrogen strategy is presented.

Язык: Английский

Процитировано

6
Room‐Temperature Synthesis of α‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction DOI
Dingguo Song, Rong Chen, Weiwei Huang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1893 - 1898

Опубликована: Фев. 29, 2024

Abstract We reported a visible‐light‐induced iron‐catalyzed α ‐alkylation of oxindoles with alcohols to offer variety ‐alkyled at room temperature. This reaction featured broad substrate scope good functional tolerance under simple conditions. Through series controlled experiments, we tried elucidated the important role light in this borrowing hydrogen (BH) reaction.

Язык: Английский

Процитировано

2
Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols DOI
Manisha Lamba,

Prasoon Raj Singh,

Tanmay

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11244 - 11260

Опубликована: Авг. 6, 2024

In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective are tunable by changing the reaction conditions. Utilization protic solvent Brønsted acid catalyst afforded C-alkylation, whereas, aprotic Lewis in good to excellent yields. Regioselectivity is achieved protecting N-center oxindole C5 alkylated product furnished exclusively. This protocol notable because it demonstrates functionalization at C7 position without need for any directing group N-center. Further, a new has been reported C-H oxygenation benzylic one derivative.

Язык: Английский

Процитировано

1
Direct Deoxygenative Homocoupling of Alcohols to Access C(sp3)–C(sp3) Bonds via Synergistic Ruthenium/Nickel Catalysis DOI
Dawei Cao, Shumei Xia, Lijuan Li

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(19), С. 14966 - 14973

Опубликована: Сен. 25, 2024

Язык: Английский

Процитировано

1
Iron and Base Catalyzed C(α)-Alkylation and One-pot Sequential Alkylation-Hydroxylation of Oxindoles with Secondary Alcohols DOI
Ratnakar Saha,

Bhairab Chand Hembram,

Surajit Panda

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6321 - 6330

Опубликована: Янв. 1, 2024

Iron-catalyzed protocol was developed for the C -alkylation of 2-oxindoles with secondary alcohols as coupling partners. Alkylated were further functionalized to 3-hydroxy-3-alkyl-2-oxindoles by using air most sustainable oxidant.

Язык: Английский

Процитировано

0
Supported Nickel Nanoparticles as Catalyst in Direct sp3 C–H Alkylation of 9H‐Fluorene Using Alcohols as Alkylating Agent DOI Creative Commons
Raju Dey,

M. Vageesh,

Harsh Joshi

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер unknown

Опубликована: Окт. 14, 2024

Abstract Herein, we report an inexpensive first‐row transition metal Ni heterogeneous catalytic system for the C sp 3 ‐mono alkylation of fluorene using alcohols as alkylating agents via borrowing hydrogen strategy. The protocol displayed versatility with high yields desired products various types primary alcohols, including aryl/hetero aryl methanols, and aliphatic agents. catalyst NPs@N−C was synthesized high‐temperature pyrolysis strategy, ZIF‐8 sacrificial template. characterized by XPS, HR‐TEM, HAADF‐STEM, XRD ICP‐MS. is stable even in air at room temperature, excellent activity could be recycled 5 times without appreciable loss its activity.

Язык: Английский

Процитировано

0
Zn(II)-Stabilized Azo-Anion Radical-Catalyzed Dehydrogenative Synthesis of Olefins DOI
Subhasree Pal, Amit Kumar Guin,

Subhankar Khanra

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 16, 2024

Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using Zn(II) complex [ZnLCl2] (1) redox-noninnocent ligand 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L), various (E)-olefins were prepared in good yields by coupling with sulfones aryl cyanides under an inert atmosphere. Under aerial atmosphere, vinyl nitriles isolated up to 82% yield reacting benzyl presence 1. Control experiments mechanistic investigation indicate active involvement aryl-azo electron hydrogen reservoir, permitting 1 perform promising catalyst.

Язык: Английский

Процитировано

0