Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Yamaguchi, Junichiro; Amaike, Kazuma; Itami, Kenichiro

doi:10.1002/9783527691920.ch16

Cited by 9 publications

(4 citation statements)

References 156 publications

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“…C–H activation is a powerful tool for the functionalization of organic compounds and an important route to pharmaceuticals and natural products A large number of such transition metal‐catalyzed transformations are enabled by directing groups . These coordinating moieties are necessary to achieve a reasonable reaction rate and regioselectivity control.…”

Section: Introductionmentioning

confidence: 99%

“…These coordinating moieties are necessary to achieve a reasonable reaction rate and regioselectivity control. However, even in the presence of a directing group, the transition metal‐catalyzed C–H functionalization requires an elevated temperature and a prolonged reaction time , . Examples of such transformations proceeding at room temperature or over a short period of time are scarce .…”

Section: Introductionmentioning

confidence: 99%

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Palladium‐Catalyzed 2‐(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

et al. 2020

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The 2‐(neopentylsulfinyl)aniline directing group that promotes rapid palladium‐catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis‐functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1‐substituted cyclopropanols were employed as equivalents of vinyl ketones.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed 2‐(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

et al. 2020

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“…Transition-metal-catalyzed C–H bond functionalization is now recognized as one of the potential synthetic strategies for the synthesis of useful compounds . In fact, recent reports indicate that C–H bond functionalization is used as a key step for the synthesis and late stage diversification of natural products, bioactive compounds, and functionalized materials .…”

mentioning

confidence: 99%

Rh(III)-Catalyzed Reaction of α-Carbonyl Sulfoxonium Ylides and Alkenes: Synthesis of Indanones via [4 + 1] Cycloaddition

2020

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The synthesis of indanone derivatives by the Rh(III)-catalyzed reaction of α-carbonyl sulfoxonium ylides with activated alkenes is reported. The reaction shows a high tolerance for functional groups and furnishes a variety of substituted indanone derivatives via a formal [4 + 1] cycloaddition. Highly stable sulfoxonium ylides were used as substrates in this C–H functionalization, and their bifunctional character could be effectively exploited using Rh(III) catalysis via sequential double C–C bond formation. Based on mechanistic studies including deuterium-labeling experiments, the reaction is proposed to proceed as follows: Rh(III)-catalyzed C–H oxidative alkenylation via β-hydride elimination, readdition of H–Rh species, a 1,2-carbon shift with the elimination of DMSO, and protonation.

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“…Over the past decades, transition-metal-catalyzed reactions have shaped contemporary organic synthesis by enabling direct functionalization of unreactive C–H bond and successfully been executed in the synthesis and late-stage functionalization of various natural products. − We envisioned that implementation of this step- and atom-economic technology for syntheses of aforementioned molecules would be very effective. Accordingly, a retrosynthetic plan was conceived (Figure ).…”

mentioning

confidence: 99%

Directed C–H Bond Functionalization: A Unified Approach to Formal Syntheses of Amorfrutin A, Cajaninstilbene Acid, Hydrangenol, and Macrophyllol

et al. 2018

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Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Cited by 9 publications

References 156 publications

Palladium‐Catalyzed 2‐(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

Palladium‐Catalyzed 2‐(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

Rh(III)-Catalyzed Reaction of α-Carbonyl Sulfoxonium Ylides and Alkenes: Synthesis of Indanones via [4 + 1] Cycloaddition

Directed C–H Bond Functionalization: A Unified Approach to Formal Syntheses of Amorfrutin A, Cajaninstilbene Acid, Hydrangenol, and Macrophyllol

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