Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions

Xia, Zhouhui; Xu‐Xu, Qing‐Feng; Zheng, Chao; You, Shu‐Li

doi:10.1039/c8cs00436f

Cited by 289 publications

(86 citation statements)

References 74 publications

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“…The substrates with electron-donating groups or electron-withdrawing groups at the C5-position were all suitable for such a reaction to deliver the desired products in moderate to good yields. Many kinds of functional groups, such as methoxyl (14), fluoro (15), chloro (16), bromo (17), and ester group (18), were all tolerated well. The substrates bearing fluoro (19) and methoxyl (20) group at C6position also worked well.…”

Section: Resultsmentioning

confidence: 99%

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Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

et al. 2020

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Catalytic reductive coupling of two electrophiles and one unsaturated bond represents an economic and efficient way to construct complex skeletons, which is dominated by transitionmetal catalysis via two electron transfer. Herein, we report a strategy of visible-light photoredox-catalyzed successive single electron transfer, realizing dearomative arylcarboxylation of indoles with CO 2. This strategy avoids common side reactions in transition-metal catalysis, including ipso-carboxylation of aryl halides and β-hydride elimination. This visible-light photoredox catalysis shows high chemoselectivity, low loading of photocatalyst, mild reaction conditions (room temperature, 1 atm) and good functional group tolerance, providing great potential for the synthesis of valuable but difficultly accessible indoline-3-carboxylic acids. Mechanistic studies indicate that the benzylic radicals and anions might be generated as the key intermediates, thus providing a direction for reductive couplings with other electrophiles, including D 2 O and aldehyde.

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Section: Resultsmentioning

confidence: 99%

“…Dearomatization of (hetero)arenes is an efficient and powerful method to provide 3D cyclic skeletons, which exist widely in pharmaceuticals and bioactive natural products [12][13][14][15][16] . Dearomative functionalization of indoles are particularly interesting to generate important indolines 15,16 .…”

mentioning

confidence: 99%

Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

et al. 2020

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“…Among the several methodologies, currently utilized in asymmetric organocatalysis, the use of chiral phosphate‐based Brønsted acids (BAs) is facing growing credit due to their wide applicability organic transformations …”

Section: Organocatalytic Dearomatization Of Naphtholsmentioning

confidence: 99%

Recent Advances in the Catalytic Dearomatization of Naphthols

Bandini

2020

Eur J Org Chem

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The catalytic dearomatization of naphthols offers a unique platform to rapidly access structurally complex and densely functionalized molecular architectures. Thermodynamically more favorable, with respect to the analogous phenol‐variant, the transformation of the phenolic ring into the corresponding naphthalenone (cited here as naphthyl dearomatization) has faced a considerable amount of attention over the past decade with constant improvements towards stereocontrol. A collection of the most representative and recent catalytic variants involving carbon–carbon as well as carbon–heteroatom bond forming events are presented in this Minireview article.

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“…Dearomatization is an important reaction for the transformations of readily available planar aromatic compounds into complex 3-dimentional structures such as spirocycles, polycycles and bridged-cycles. [1][2][3][4][5] Recently, transition-metal-catalyzed dearomatization reaction of furans, pyrroles, indoles, pyridines, phenols, anilines, and naphthols, have been developed as powerful strategies to construct complex structures, [6][7][8][9][10][11][12][13][14][15] and catalytic asymmetric dearomatization has becoming an emerging concept in organic synthesis. 16 However, due to the inherent stability and high resonance energy of nonactivated arenes, the dearomative transformation of the nonactivated arenes remains an important challenge.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Asymmetric Domino Heck/Carbocyclization/Suzuki Reaction: A Dearomatization of Nonactivated Naphthalenes

Chen

Wang

et al. 2021

CCS Chem.

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We report herein a novel Pd-catalyzed asymmetric domino Heck-carbocyclization-Suzuki reaction of N-(2-bromoaryl)-2-naphthylacrylamides. The reaction involves a novel and enantioselective dearomative 1,2insertion of naphthalene group, thus providing an unique dearomatization strategy of nonactivated naphthalenes. A new phosphoramidite ligand L12 which displayed excellent reactivity and enantioselectivity in the reaction has been developed. The reaction employs readily available starting materials, and provides straightforward access to a diverse array of spirooxindoles bearing three stereogenic centers in high yields under mild conditions.

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Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions

Abstract: We summarize in this review the recent development of chiral phosphoric acid (CPA)-catalyzed asymmetric dearomatization reactions.

Cited by 289 publications

References 74 publications

Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis

Recent Advances in the Catalytic Dearomatization of Naphthols

Palladium-Catalyzed Asymmetric Domino Heck/Carbocyclization/Suzuki Reaction: A Dearomatization of Nonactivated Naphthalenes

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