Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Gujjarappa, Raghuram; Vodnala, Nagaraju; Garg, Aakriti; Hazra, Chinmoy Kumar; Gupta, Shikhar; Malakar, Chandi C.

doi:10.1002/slct.201904059

Cited by 6 publications

(3 citation statements)

References 73 publications

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“…In most cases, literature reports reveal the requirement for a base/metal in the reaction when phenylboronic acid reacts with reactive oxygen species. 22 The mechanism of the reaction is ambiguous, particularly in light of the fact that the reaction can occur in the absence of any base/metal under air. Via control experiments, we have already confirmed that a radical process might be involved in the transformation.…”

Section: Resultsmentioning

confidence: 99%

The graphite-catalyzed ipso-functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

et al. 2021

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Section: Resultsmentioning

confidence: 99%

The graphite-catalyzed ipso-functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

et al. 2021

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“…An ortho-substituted phenol 9 was obtained as a result of amino acid mediated aerobic oxidation of the corresponding boronic ester 8h. 12 In conclusion, we have reported the utilization of anion−π interactions between carbonate anions and easily accessible aryl halides for the synthesis of aryl phosphonates and aryl boronates. The photoinduced C−X activation pathway operates via a radical mechanism initiated by an intrasystem SET.…”

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confidence: 88%

“…Similarly, with a phenyl substituent, 43% of the desired product was obtained (when X = Br) that increased to 65% in the case of the iodo substituent (Scheme , product 8g ). An ortho -substituted phenol 9 was obtained as a result of amino acid mediated aerobic oxidation of the corresponding boronic ester 8h …”

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confidence: 99%

Light-Induced Activation of C–X Bond via Carbonate-Assisted Anion−π Interactions: Applications to C–P and C–B Bond Formation

Roy

2023

Org. Lett.

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We have presented a carbonate anion assisted photochemical protocol for the C–X bond activation. Anion−π interactions have been leveraged to generate aryl radicals from easily accessible aryl halides that are further utilized in C–P and C–B bond formation reactions with excellent reactivity and broad functional group tolerance. Spectroscopic investigations and DFT studies were conducted for mechanistic insights. This inexpensive method alleviates the use of a photocatalyst and the need of preactivation of the substrate for the light-induced activation of C–X bonds.

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A Facile C‐H Insertion Strategy using Combination of HFIP and Isocyanides: Metal‐Free Access to Azole Derivatives

et al. 2020

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An efficient metal-free approach has been devised towards the synthesis of azoles via CÀ H insertion protocol. Various isocyanides were examined as effective C1-synthons. The HFIP plays crucial role as hydrogen source and promoter of the reaction in order to reveal the maximum efficacies to accomplish the transformation in high yields of the products with excellent functional group tolerance. The control experiment affirmed 83% of deuterium incorporation, when the reaction was performed using HFIP-d 2. Isocyanides are witnessed as significant building blocks in synthetic organic chemistry [1] because of their ability for the reaction with various electrophiles, nucleophiles and radicals. [2] These molecules are also found as benign CO surrogates, ligands in metal complexes and as C1 sources in formal cycloaddition reactions towards the synthesis of valuable targets. [1f-h,2À 3] Furthermore, isocyanides have been extensively explored in engineering a broad spectrum of N-heterocycles. [1a] A large number of useful reports have been noticed on isocyanide insertion owing to their reactivities and efficiencies. In literature, it has been shown that the isocyanides have been utilized as CÀ NÀ C, [4-9] CÀ N [10-12] and C1-source [13-15] to construct various complex molecules (Scheme 1). Further, the reported methodologies are mainly concerned on using the transition metals such as Pd, [4,13,15] Cu, [5,11] Co [6] and Ni. [7,14] In recent years, the isocyanide insertion strategy under non-metal, Lewis-acid, base and photocatalyzed reaction conditions become familiar in the field of organic synthesis. [8,12] It is noteworthy that the isocyanide insertion chemistry under transition metal-free and non-transition metal-free conditions are very rare and remained asserting task for the synthetic chemists. [8-12] In particular, utilizing isocyanides as C1-source has always been explored under transition metal-catalysis. [13-15] In view of this, during our continuous efforts on identifying the transition metal-free catalyzed transformations, [16] we have [a

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Amino‐Acid‐Mediated Aerobic Oxidation of Organoborons for the Synthesis of Phenolic Derivatives Using Single Electron Transfer

Cited by 6 publications

References 73 publications

The graphite-catalyzed ipso-functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

The graphite-catalyzed ipso-functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Light-Induced Activation of C–X Bond via Carbonate-Assisted Anion−π Interactions: Applications to C–P and C–B Bond Formation

A Facile C‐H Insertion Strategy using Combination of HFIP and Isocyanides: Metal‐Free Access to Azole Derivatives

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