Nickel‐Catalysis Enabling α‐Alkylation of Ketones by Secondary Alcohols DOI

Amreen K. Bains,

Ayanangshu Biswas, Abhishek Kundu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(16), P. 2815 - 2821

Published: July 11, 2022

Abstract The α‐alkylation of ketones utilizing a secondary alcohol has been accomplished by an isolable, bench‐stable, inexpensive nickel catalyst affording high yields β,β‐disubstituted products. This report contributes in the pool few scarce examples base metal discovered for this purpose. substrate scope can span wide range including aliphatic, alicyclic, and cyclic alcohols. Functionalization cholesterol molecule is also possible following methodology. interconvert between azo hydrazo form reversible fashion to enable chemical transformation. magnified image

Language: Английский

Recent advances in C/N-alkylation with alcohols through hydride transfer strategies DOI
Mahdi Jafarzadeh,

Seyed Hasan Sobhani,

Karol Gajewski

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(39), P. 7713 - 7745

Published: Jan. 1, 2022

Recent advances in C/N alkylation using alcohols as alkylating reagents via hydrogen-shuttle methodologies: Borrowing Hydrogen, Acceptorless Dehydrogenative Coupling, and Base-mediated Hydride Transfer.

Language: Английский

Citations

20

A strategic approach for Csp3–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach DOI
Rahul Sharma, Avijit Mondal,

Arup Samanta

et al.

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(3), P. 611 - 617

Published: Jan. 1, 2023

Herein, we described the selective synthesis of both alkylated and alkenylated fluorenes using a single SNS ligand derived nickel complex.

Language: Английский

Citations

12

Bis-Triazolylidenes of Manganese and Rhenium and Their Catalytic Application in N-Alkylation of Amines with Alcohols DOI Creative Commons
Sofia Friães, Clara S. B. Gomes, Beatriz Royo

et al.

Organometallics, Journal Year: 2023, Volume and Issue: 42(14), P. 1803 - 1809

Published: April 11, 2023

A new family of air-stable Mn and Re complexes bearing bidentate bis(1,2,3-triazol-5-ylidene) ligands with the general formula [M(bis-triazolylidene)(CO)3X] (M = or Re; X Cl Br), containing a methylene linker direct link between two triazolylidene ligands, is presented. All have been applied as catalysts for N-alkylation anilines benzylic alcohols. The complex bis-triazolylidene bridge fragments was shown to be highly efficient catalyst, affording corresponding amine in 92% yield presence low base loading (t-BuOK, 0.1 equiv). Comparison imidazolium- triazolium-derived N-heterocyclic carbene showed that triazolylidenes displayed higher catalytic activity when used.

Language: Английский

Citations

11

Chemoenzymatic Catalysis: Cooperativity Enables Opportunity DOI
Logan Hessefort, Lauren J. Harstad,

Kayla R. Merker

et al.

ChemBioChem, Journal Year: 2023, Volume and Issue: 24(14)

Published: May 30, 2023

The application of enzymes in synthetic organic chemistry has emerged as a powerful means to generate molecular complexity highly selective, efficient, and sustainable manner. While have increasingly been incorporated into sequences for numerous academic industrial applications on their own sequential processes, utility cooperative catalysis with small molecule catalytic platforms recently drawn increased attention across the field synthesis. In this review, we present selection notable accomplishments chemoenzymatic provide perspective its future directions.

Language: Английский

Citations

11

Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles DOI
Fatemeh Doraghi,

Farzad Gilaninezhad,

Somaye Karimian

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

Citations

4

CuO NPs catalyzed synthesis of quinolines, pyridines, and pyrroles via dehydrogenative coupling strategy DOI
Shivangi Gupta, Ankur Maji, Dibyajyoti Panja

et al.

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 413, P. 1017 - 1027

Published: Aug. 13, 2022

Language: Английский

Citations

18

Well-defined manganese complex catalyzed dehydrogenative synthesis of quinazolin-4(3H)-ones and 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides DOI

Debjyoti Pal,

Avijit Mondal, Dipankar Srimani

et al.

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(10), P. 3202 - 3208

Published: Jan. 1, 2022

The synthesis of N-heterocycles has been considered an emerging topic chemical research due to its widespread usage in medicinal chemistry, materials science, and natural product synthesis.

Language: Английский

Citations

18

Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols DOI
Pennamuthiriyan Anandaraj, Rengan Ramesh

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2494 - 2504

Published: Feb. 7, 2024

We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied elemental spectroscopic (FT-IR, NMR, HRMS) analyses. solid-state molecular structure complex 2 has authenticated a single-crystal X-ray diffraction study. Furthermore, series (24 examples) utilizing 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling benzyl with benzenesulfonamide. Gratifyingly, catalytic protocol is highly selective yield up to 93% produces eco-friendly water/hydrogen gas as byproducts. control experiments plausible mechanistic investigations indicate that in situ generated aldehyde benzenesulfonamide leads desired product. In addition, large-scale one thiadiazine unveils synthetic usefulness current methodology.

Language: Английский

Citations

3

Synthesis of N-heterocycles through alcohol dehydrogenative coupling DOI
Bhaskar Paul, Dibyajyoti Panja, Sabuj Kundu

et al.

Nature Protocols, Journal Year: 2024, Volume and Issue: 19(12), P. 3640 - 3676

Published: Aug. 22, 2024

Language: Английский

Citations

3

Nickel-catalyzed sustainable synthesis of N-heterocycles through dehydrogenative coupling of alcohols DOI

Krishanu Bera,

Arup Mukherjee

Tetrahedron Letters, Journal Year: 2021, Volume and Issue: 81, P. 153326 - 153326

Published: Aug. 20, 2021

Language: Английский

Citations

21