Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates

Jiang, Lin; Li, Yong‐Gen; Li, Hang; Yuan, Ming-Wei; Chuan, Yongming; Liu, Hongli; Yuan, Minglong

doi:10.3184/174751917x14878812592652

Cited by 4 publications

(1 citation statement)

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“…The Jiang group developed a catalyst-free γ-substitution reaction of the MBH carbonates of isatins with sodium sulfinates under mild reaction conditions ( Scheme 73 ). 128 This protocol features easily accessible starting materials that are a variety of MBH carbonates of isatins and sodium arylsulfinates, which allowed the rapid synthesis of 3-alkenyloxindoles in high yields (up to 96%) and Z / E -selectivities (up to >20 : 1). Unfortunately, the MBH carbonates of isatins possessing a 5-nitro group or derived from acrylonitrile were unsuccessful because of unwanted side reactions that became dominant under the same reaction conditions.…”

Section: Applications Of Sodium Sulfinatesmentioning

confidence: 99%

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

2021

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Section: Applications Of Sodium Sulfinatesmentioning

confidence: 99%

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

2021

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Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

Chen

et al. 2019

The Chemical Record

103

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The development of synthetic protocols to access architectures with broad structural and functional diversity from readily available starting materials is very attractive in both organic and medicinal chemistry fields. Toward this objective, the multifunctional isatin‐derived Morita‐Baylis‐Hillman (MBH) adducts provide opportunities to construct a variety of complex scaffolds containing a “privileged” oxindole motif through several catalytic pathways. By forming the ammonium or phosphonium salts with Lewis bases, isatin‐derived MBH adducts can undergo allylic substitutions with a range of nucleophiles, usually in a SN2′‐SN2′ pattern. Besides, assisted by Brønsted bases, the corresponding onium salts can be converted into the allylic ylide intermediates, which can undergo various annulation reactions or even 1,3‐difunctionalizations. Moreover, recent cooperative catalysis of Lewis bases and transition metal complexes further puts forward the application of isatin‐derived MBH adducts. This tutorial review covers the significant transformations of isatin‐derived MBH adducts, mostly in an asymmetric version, catalyzed by various Lewis bases over the past decade.

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Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

2023

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Herein, a divergent and selective synthesis of (E)-3alkylidene oxindole, which is a highly valuable framework due to its presence in biologically important molecules, via palladiumcatalyzed multicomponent reaction of 3-diazo oxindole, isocyanide, and aniline has been developed. Further, the feasibility of the reaction was demonstrated by employing differently substituted 3diazo oxindoles, isocyanides, and anilines as starting material and obtaining the corresponding products in 31−83% isolated yields. Besides, a plausible mechanism has been presented and further investigated using DFT calculations which suggest the formation of the Pd-carbene complex and ketenimine intermediate as the key step during the catalytic cycle.

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Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates

Cited by 4 publications

References 35 publications

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

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Catalyst-free synthesis of 3-alkenyloxindoles from isatin-derived Morita–Baylis–Hillman carbonates

Cited by 4 publications

References 35 publications

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

Divergent and Selective Synthesis of 3-Alkylidene Oxindoles Using Pd-Catalyzed Multicomponent Reaction

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Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds