Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling

Das, Sanju; Maiti, Debabrata; Sarkar, Suman De

doi:10.1021/acs.joc.7b03198

Cited by 122 publications

(51 citation statements)

References 93 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…De Sarkar and Nanda independently reported an operationally simple procedure to prepare various polysubstituted quinolines from simple alcohol precursors (Scheme ). The acceptorless dehydrogenative process was efficiently carried out earth abundant Ni‐catalyst [Ni(MeTAA)].…”

Section: Nickel‐catalyzed Dehydrogenative Bond Formationsmentioning

confidence: 99%

Nickel‐Catalyzed Dehydrogenative Couplings

2019

View full text Add to dashboard Cite

In last decade, nickel-catalyzed organic reactions made tremendous progress due to their distinctive redox character. It has unfolded many contemporary synthetic transformations namely cross-coupling, carbon-carbon bond cleavage and directed CÀ H functionalization to achieve the targeted medicinal organic molecules in a straightforward manner. Beyond these well documented approaches, dehydrogenative coupling a challenging bond forming strategy by expelling hydrogen from unfunctionalized coupling partners is less explored. In accord with this, nickel-catalyst has been studied to perform different class of dehydrogenative coupling between easily accessible substrates. Nickel catalyzed processes for the construction of carbon-carbon, carbon-heteroatom and heteroatom-heteroatom bonds by dehydrogenation are discussed herein in a sustainable manner.[a] Dr.

show abstract

Section: Nickel‐catalyzed Dehydrogenative Bond Formationsmentioning

confidence: 99%

Nickel‐Catalyzed Dehydrogenative Couplings

2019

View full text Add to dashboard Cite

show abstract

“…In our ongoing research program towards the sustainable synthesis of heteroaryl compounds, [16] we envisioned base-promoted aerial oxidation [17] followed by homolytic aromatic substitution cascade for the synthesis of phenanthridine derivatives (Scheme 1b). This transition metal-free approach would allow the direct use of alcohols [18] and 2-iodoaniline derivatives.…”

Section: Abstract: Phenanthridine; Radical; Aerobic Oxidation; Homogementioning

confidence: 99%

“…[13] In 2011, Bin Li first synthesized phenanthridines from imine substrate using Pd-catalyzed intramolecular CÀ H activation/CÀ C cross-coupling, [14] subsequently Kwong group reported a transition-metal-free procedure. In our ongoing research program towards the sustainable synthesis of heteroaryl compounds, [16] we envisioned base-promoted aerial oxidation [17] followed by homolytic aromatic substitution cascade for the synthesis of phenanthridine derivatives (Scheme 1b). In our ongoing research program towards the sustainable synthesis of heteroaryl compounds, [16] we envisioned base-promoted aerial oxidation [17] followed by homolytic aromatic substitution cascade for the synthesis of phenanthridine derivatives (Scheme 1b).…”

mentioning

confidence: 99%

Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

Halder

Sarkar

2019

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a CÀ N bond formation followed by a radical CÀ C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield.

show abstract

“…This protocol involves the reaction of both primary/secondary α-2aminoaryl alcohols (221) either with ketones (222)/secondary alcohols (223) and occurred through C-N and C-C bonds formations using low catalytic loading (Scheme 83). 111 This pathway is cost-effective, efficient and has good substrate scope to afford excellent yield of products. Further, the method is utilized to synthesize series of wide range of substituted quinolines.…”

Section: Various Approaches For the Synthesis Of Quinolines And Theirmentioning

confidence: 99%

A review on transition-metal mediated synthesis of quinolines

2018

View full text Add to dashboard Cite

Quinoline is one of the important class of heterocyclic compounds which have gained considerable importance because of its high pharmaceutical efficacy and broad range of biological activities such as anticancer, anti-malarial, anti-microbial and anti-asthmatic. As a consequence, the desire for new versatile and efficient route for the synthesis of quinoline scaffolds remains an active and growing area of interest both in academia and industry. However, developments of transition-metal catalyzed synthetic methods have witnessed a dominant position over the past few years for the synthesis of diverse range of complex heterocyclics containing quinoline scaffolds. This review specifically provides an overview of the literature available on the transitionmetal catalyzed synthetic methodologies for the synthesis of polysubstituted quinoline derivatives.

show abstract

Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling

Cited by 122 publications

References 93 publications

Nickel‐Catalyzed Dehydrogenative Couplings

Nickel‐Catalyzed Dehydrogenative Couplings

Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

A review on transition-metal mediated synthesis of quinolines

Contact Info

Product

Resources

About