Iodine-Mediated Intramolecular C–H Amination of Benzimidazoles: A Metal-Free Route to Dihydroimidazobenzimidazoles

De, Prithwiraj; Pradhan, Sourav; Shah, Tariq; Punniyamurthy, Tharmalingam

doi:10.1055/s-0036-1591568

Cited by 6 publications

References 1 publication

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Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Ghosh

Chattopadhyay

2019

Adv Synth Catal

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A metal‐free synthesis of a range of 4‐aryl‐2‐quinolone derivatives has been developed which utilizes an iodine‐mediated intramolecular C−H amidation of 3,3‐diarylacryl amides as the key step. Electron‐withdrawing or ‐donating substituents in either of the aryl rings display marginal influence on the course of the reaction. However, the presence of the diarylalkene moiety has been found to be crucial for the success of the reaction. The reaction proceeds in very good yield and is applicable to a range of substrates. Moreover, the methodology overcomes some of the difficulties associated with metal‐mediated approaches such as regio‐isomeric product formation, and E‐Z isomerization. We propose a mechanism involving the in situ generation of hypoiodous acid as source of positive iodine.magnified image

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Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Ghosh

Chattopadhyay

2019

Adv Synth Catal

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Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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The progress in CÀ N bond construction is significant in synthetic and biological chemistry. Cross-dehydrogenative couplings of CÀ H and NÀ H motifs serve as a unique class of the most atom-economical and straightforward strategies for constructing CÀ N bonds. Herein, we enclosed the most updated methodologies developed in the assembly of CÀ N bonds via photo-catalyzed, transition-metal-catalyzed, electrochemical, and metal-free amination and amidation reactions of saturated and unsaturated CÀ H bonds. Compared with the well-established transition-metal-catalyzed protocols, electricity, or visible light-mediated amination and amidation reactions are competent and appealing. Plausible mechanistic pathways are also described in representative amidation and amination reactions to provide insights for the future development of environmentally kind processes.

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PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

Bhowmick

Brahmachari

2023

Eur J Org Chem

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An efficient and straightforward protocol for accessing a new series of functionalized 4-aminocoumarins from PIDA/I 2 -mediated decarboxylative C 4 -amination of coumarin-3-carboxylic acids via direct C sp2 À H dehydrogenative CÀ N cross-coupling with secondary amines under ambient conditions has been accomplished. The notable advantages of this protocol are the tolerance of diverse functional groups, mild reaction conditions at ambient temperature, moderate to good yields, short reaction times (in minutes), high regioselectivity, gram-scale applicability, and eco-friendliness. This is the first report of decarboxylative C sp2 À H cross-dehydrogenative CÀ N coupling of coumarin-3-carboxylic acids for synthesizing 4-aminocoumarins.

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Iodine-Mediated Intramolecular C–H Amination of Benzimidazoles: A Metal-Free Route to Dihydroimidazobenzimidazoles

Cited by 6 publications

References 1 publication

Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

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Iodine-Mediated Intramolecular C–H Amination of Benzimidazoles: A Metal-Free Route to Dihydroimidazobenzimidazoles

Cited by 6 publications

References 1 publication

Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Metal‐Free Synthesis of 4‐Aryl‐2‐quinolone Derivatives by Iodine‐Mediated Intramolecular C−H Amidation

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

PhI(OAc)2/I2‐Mediated Decarboxylative C4‐Amination of Coumarin‐3‐Carboxylic Acids via Csp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions

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PhI(OAc)₂/I₂‐Mediated Decarboxylative C₄‐Amination of Coumarin‐3‐Carboxylic Acids via C_sp2−H Dehydrogenative C−N Cross‐Coupling under Ambient Conditions