One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature

Ahammed, Sabir; Nandi, Shiny; Kundu, Debasish; Ranu, Brindaban C.

doi:10.1016/j.tetlet.2016.02.097

Cited by 40 publications

(22 citation statements)

References 63 publications

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“…[6] However,a ll these valuable methods require at ransition metal catalyst, al igand and as toichiometric amount of ab ase.T oo ur knowledge,m etal and additive-free radical borylation of alkyl halides with diborons is unknown. [7] Arylboronates can be obtained from haloarenes and diborons via reactive aryl radicals [8][9][10][11][12][13] (Scheme 1B). Along these lines,Marder developed azinc(II)-catalyzed borylation of aryl halides using astoichiometric base [8] and photoinduced aryl halide borylation was reported by Larionov, [9] Li [10] and Fu.…”

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confidence: 99%

Metal‐Free Radical Borylation of Alkyl and Aryl Iodides

2018

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A metal‐free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B 2 cat 2 ) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C‐radical borylation with B 2 cat 2 are disclosed.

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confidence: 99%

Metal‐Free Radical Borylation of Alkyl and Aryl Iodides

2018

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“…At the outset, we carried out the reactions under the reaction conditions that were similar to the previously reported Sandmeyer-type borylation reactions [47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62], with MeCN as the solvent. We chose 4-methoxyl aniline as the starting material, and no target product could be observed under the classical reaction conditions [ t -BuONO, MeCN, room temperature].…”

Section: Resultsmentioning

confidence: 99%

Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

Ding

Zhu

et al. 2019

Molecules

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A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim products selectively. This conversion tolerated a series of functional groups, including chloro, bromo, fluoro, ester, hydroxy, cyano and amide.

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“…Combining the work of Wang's group and our work, Ranu and co‐workers reported the “one‐pot” visible light photocatalyzed borylation of arylamines in the presence of tert ‐butyl nitrite at room temperature (Scheme ) . The procedure avoids the isolation and handling of hazardous diazonium salts.…”

Section: Borylation Of Arylamine Derivativesmentioning

confidence: 99%

Recent Advances in C–B Bond Formation through a Free Radical Pathway

Yan

Huang

2017

Adv Synth Catal

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The development of a methodology for the preparation of arylboronic acids or arylboronates is of significant interest to organic chemists. Classical synthetic methods to prepare these organoboron compounds are based on the reaction of Grignard or lithium reagents with trialkyl borates. In the past few decades, the transition‐ metal‐catalyzed borylation of aryl halides, or pseudohalides, and C–H bonds of hydrocarbons has been a powerful tool for the synthesis of arylboronates in modern organic synthesis. These transformations are generally considered to proceed via organometallic intermediates generated by oxidative addition or transmetalation processes from the boron reagent. Several reviews on this type of borylation catalyzed by transition metals have been published in the literature. Interestingly, there has been a novel recognition that the boron reagent can participate in free‐radical coupling via the homolytic cleavage of the boron‐boron bond in recent years. In this review, recent advances in this new area of boron chemistry are summarized and the reaction mechanisms are also discussed.

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One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature

Cited by 40 publications

References 63 publications

Metal‐Free Radical Borylation of Alkyl and Aryl Iodides

Metal‐Free Radical Borylation of Alkyl and Aryl Iodides

Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

Recent Advances in C–B Bond Formation through a Free Radical Pathway

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