Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors

Chen, Xiuwen; Yang, Zhihai; Chen, Xuyan; Liang, Wanyi; Zhu, Zhongzhi; Xie, Feng; Li, Yibiao

doi:10.1021/acs.joc.9b02558

Cited by 18 publications

(15 citation statements)

References 48 publications

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“…A hydrogen-transfer-mediated cross-coupling reaction can also be used for the preparation of N -arylindoles ( Scheme 16 ) [ 73 ]. The starting material, as represented by the structure of substituted indolines S16-1 , reacts with 2-naphthols and their derivatives in the presence of Pd/C and sodium methoxide.…”

Section: Transition-metal-catalyzed N -Arylation Of Indolesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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Section: Transition-metal-catalyzed N -Arylation Of Indolesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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“…Despite these advances, the utilization of ammonium formate as cost-effective reductant and eco-friendly water as solvent to achieve mono/dual amination and cyclization of phenols remains unexplored. Owing to our ongoing interest in hydrogen-transfer reactions, we recently reported an N -arylation transformation in which indoline reactants were treated as hydrogen donors through hydrogen-transfer-mediated activation . Inspired by this work, here we report a green and efficient approach to synthesize aryl amines from phenols and amines via a direct aqueous hydrogen-transfer coupling.…”

mentioning

confidence: 99%

“…Owing to our ongoing interest in hydrogen-transfer reactions, 14 we recently reported an N-arylation transformation in which indoline reactants were treated as hydrogen donors through hydrogen-transfer-mediated activation. 15 Inspired by this work, here we report a green and efficient approach to synthesize aryl amines from phenols and amines via a direct aqueous hydrogen-transfer coupling.…”

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confidence: 99%

Mono/Dual Amination of Phenols with Amines in Water

et al. 2020

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We herein describe a practical direct amination of phenols through a palladium-catalyzed hydrogen-transfer-mediated activation method to synthesize the secondary and tertiary amines. In this conversion, environmentally friendly water and inexpensive ammonium formate were used as solvent and reductant, respectively. A range of amines, including aliphatic amines, aniline, secondary amines, and diamines, could be coupled effectively by this method to achieve mono/dual amination and cyclization of phenols. This study not only provides a green and mild strategy for the synthesis of secondary and tertiary naphthylamines but also expands the synthesis of chloroquine in organic chemistry.

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“…373 Based on an identical approach, in 2019, the Chen and Zhu groups reported a N-arylation of naphthols with indoline as both amine and hydride sources (Scheme 209c). 374 In the same year, Li's group employed HCO 2 NH 4 as both a hydride donor and an amine source to convert phenols to diaryl amines catalyzed by Pd/C (Scheme 209d). 375 In 2020, the same group developed a carbazole synthesis protocol via amination of 2,2′-biphenols by double C(Ar)−OH bond cleavage with ammonia as the amine source catalyzed by Pd(OH) 2 /C (Scheme 209e).…”

Section: Phenols and Aryl Ethers Utilized As Formal Aryl Electrophile...mentioning

confidence: 99%

Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage

2020

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Employing phenols and phenol derivatives as electrophiles for cross-coupling reactions has numerous advantages over commonly used aryl halides in terms of environmental-friendliness and sustainability. In the early stage of discovering such transformations, most efforts have been devoted to utilizing highly activated sulfonate types of phenol derivatives (e.g., OTf, OTs, etc.), which have similar reactivities to the corresponding aryl halides. However, a continuing scientific challenge is how to achieve the direct C–O functionalizations of relatively less-activated phenol derivatives more efficiently. In this review, we will focus on the recent updates on the C–O functionalizations of less-activated phenol derivatives, from aryl carboxylates (e.g., pivalates, acetates, etc.), aryl carbamates and carbonates, to aryl ethers (anisoles, diaryl ethers, aryl pyridyl ethers, aryl silyl ethers), to phenolate salts, and ultimately to simply unprotected phenols, sorted by the types of bond formations. Both transition-metal-catalyzed and transition-metal-free protocols will be covered and discussed in detail. Instead, the C–O functionalizations of aryl sulfonates will not be covered extensively unless they are closely related, due to their high reactivity. Since aryl ethers and phenols represent the main linkages or units in lignin biomass, the successes of such transformations will potentially make major contributions to the direct lignin biomass upgrading and depolymerization.

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Hydrogen-Transfer-Mediated N-Arylation of Naphthols Using Indolines as Hydrogen Donors

Cited by 18 publications

References 48 publications

Recent Progress Concerning the N-Arylation of Indoles

Recent Progress Concerning the N-Arylation of Indoles

Mono/Dual Amination of Phenols with Amines in Water

Transformations of Less-Activated Phenols and Phenol Derivatives via C–O Cleavage

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