Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and <i>N</i>‐(<i>ortho</i>‐Chloromethyl)aryl Amides

Yang, Qing‐Qing; Xiao, Cong; Lu, Liang‐Qiu; An, Jing; Tan, Fang; Li, Bin‐Jie; Xiao, Wen‐Jing

doi:10.1002/anie.201203657

Cited by 141 publications

(38 citation statements)

References 128 publications

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“…In the past several years, we are interested in carbo-and heterocycle synthesis by using acyl-stabilized sulphur ylides 12,15,16,[27][28][29] . We herein describe an unprecedented Pdcatalysed DC reactions of vinyl benzoxazinanones by using sulphur ylides to highly enantioselectively trap Pd-stabilized zwitterionic intermediates I (Fig.…”

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confidence: 99%

Asymmetric trapping of zwitterionic intermediates by sulphur ylides in a palladium-catalysed decarboxylation-cycloaddition sequence

Tan

et al. 2014

Nat Commun

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Through nearly 50 years of development, sulphur ylides have been established as versatile and powerful reagents for the construction of carbocycles and heterocycles. Despite advances, two important and yet elusive bottlenecks continue to inhibit the advancement of this chemistry: a limited number of reagents with polar groups to react with sulphur ylides, and the wide utilization of chiral auxiliaries or substrates to achieve asymmetric cycloaddition processes in the majority of known reports. Herein, we apply an asymmetric palladium catalysis strategy to the chemistry of sulphur ylides to address these two fundamental problems. We thus achieve an unprecedented decarboxylation-cycloaddition sequence of cyclic allylic esters with sulphur ylides through the enantioselective trapping of Pd-stabilized zwitterionic intermediates by the ylides. As a result, a series of biologically and synthetically important 3-vinyl indolines are rapidly assembled with a high reaction efficiency and stereoselectivity.

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confidence: 99%

Asymmetric trapping of zwitterionic intermediates by sulphur ylides in a palladium-catalysed decarboxylation-cycloaddition sequence

Tan

et al. 2014

Nat Commun

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157

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“…[13],[14] Several strategies to generate and intercept A o -QMs have been reported, including photochemical fragmentation, [15] fluoride induced elimination of ammonium salts, [16] pyrolysis of o- hydroxymethyl anilines, [17] and Brønsted base-induced elimination. [18] …”

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confidence: 99%

N‐Heterocyclic‐Carbene‐Catalyzed Synthesis of 2‐Aryl Indoles

et al. 2014

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A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.

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“…Aza-o-quinone methide (1) and its analogues are important and unstable intermediates. [6][7][8][9][10][11][12][13][14][15][16][17] They may carry out [4 + 1], [6][7][8] [4 + 2] [9][10][11][12][13] and [4 + 3] [14] cycloadditions to form tetrahydroquinolines, [9,[11][12][13] quinolines, [9,10] indoles [6][7][8] and benzotriazepine, [14] which are useful scaffolds to build many drugs and natural products, [9] such as virantmycin, [15] and chartellin. [16] Interestingly, to carry out the cycloaddition reactions, in-situ generated 1 needs to be in alkaline conditions, instead of acidic conditions.…”

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confidence: 99%

Aza‐ortho‐Quinone Methide and Its Conjugated Acid: Reactivity, Stability and Acidity

Sung

et al. 2020

ChemPhysChem

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Aza‐o‐quinone methides and their conjugated acids are reactive drug metabolites that might react with nucleophilic sites of DNAs and proteins to cause cancer or immune responses, and their reactivity with water is the key information to judge if these metabolites are harmful in living systems. For the first time, aza‐o‐quinone methide (1) and its conjugated acid (2) are observed by laser flash photolysis, and their reactivity, stability and acidity in water are determined.

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Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

Abstract: Batting the ylides: A simple procedure carried out under mild conditions allows the direct and efficient synthesis of structurally diverse indoles. This approach involves a cascade reaction of sulfur ylides and N-(ortho-chloromethyl)aryl amides.

Cited by 141 publications

References 128 publications

Asymmetric trapping of zwitterionic intermediates by sulphur ylides in a palladium-catalysed decarboxylation-cycloaddition sequence

Asymmetric trapping of zwitterionic intermediates by sulphur ylides in a palladium-catalysed decarboxylation-cycloaddition sequence

N‐Heterocyclic‐Carbene‐Catalyzed Synthesis of 2‐Aryl Indoles

Aza‐ortho‐Quinone Methide and Its Conjugated Acid: Reactivity, Stability and Acidity

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