Palladium-Catalyzed Oxidative Allylic C−H Silylation

Larsson, Johanna M.; Zhao, Tony S. N.; Szabó, Kálmán J.

doi:10.1021/ol200445b

Cited by 72 publications

(67 citation statements)

References 49 publications

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“…In 2011, Szabó and coworkers [31] disclosed the first Pdcatalyzed oxidative allylic C-H bond silylation with hexamethyldisilane as the silylation reagent (Scheme 30). The reaction used the hypervalent iodine(III) reagent as the most efficient oxidant thus a hydrogen scavenger being not necessary.…”

Section: )-H Bondsmentioning

confidence: 99%

Direct silylation reactions of inert C-H bonds via transition metal catalysis

Yang

Wang

2015

Sci. China Chem.

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In the past thirty years, transition metal catalyzed silylation of inert C-H bonds has attracted intensive attention due to the importance and wide use of organosilicon compounds. In this review, the silylation reactions of inert C-H bonds catalyzed by transition metal complexes of Ir, Rh, Ru, Pt, Pd, Ni, and Sc, and the strategies utilized to access the site-selective C-H silylation products have been summarized. Furthermore, the mechanisms of C-H silylation reactions have been discussed briefly. transition metal, inert C-H bond, catalysis, silylation, regioselectivity

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Section: )-H Bondsmentioning

confidence: 99%

Direct silylation reactions of inert C-H bonds via transition metal catalysis

Yang

Wang

2015

Sci. China Chem.

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“…Later, the same research group developed the first Pd-catalyzed oxidative allylic C–H silylation of terminal olefins 102 using hexamethyldisilane 104 as the silyl source (Larsson et al, 2011 ). This catalytic process employs hypervalent iodine(III) reagent PhI(OCO(4-NO 2 C 6 H 4 )) 2 105 as an oxidant and Pd(OAc) 2 or nitrogen and selenium-based palladium catalyst 103 ( Scheme 12B ).…”

Section: C–b and C–si Bond Formationmentioning

confidence: 99%

Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions

Shetgaonkar

Singh

2020

Front. Chem.

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Hypervalent iodine compounds are valuable and versatile reagents in synthetic organic chemistry, generating a diverse array of useful organic molecules. Owing to their non-toxic and environmentally friendly features, these reagents find potential applications in various oxidative functionalization reactions. In recent years, the use of hypervalent iodine reagents in palladium-catalyzed transformations has been widely studied as they are strong electrophiles and powerful oxidizing agents. For instance, extensive work has been carried out in the field of C–H bond functionalization via Pd-catalysis using hypervalent iodine reagents as oxidants. In addition, nowadays, iodine(III) reagents have been frequently employed as arylating agents in Pd-catalyzed C–H arylation or Heck-type cross-coupling reactions. In this review, recent advancements in the area of palladium-catalyzed oxidative cross-coupling reactions using hypervalent iodine reagents are summarized in detail.

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“…14 Catalytic versions of this chemistry, first developed by White and co-workers, are particularly attractive, as excellent selectivity for either branched or linear product can be achieved through an appropriate choice of ligand, and a wide range of nucleophilic functional groups can be introduced. 15,16 Further investigations on palladium-based systems have resulted in the development of a myriad of impressive C-O, C-N, C-Si, 17 C-B, 18 and C-C bond-forming reactions. 19 More recently, Nakamura and co-workers reported an iron-based system for nucleophilic arylation of olefins with Grignard reagents by using mesityl iodide as a mild stoichiometric oxidant.…”

Section: Synpacts Synlett Allylic C-h Functionalizationmentioning

confidence: 99%

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

Durham¹,

Wang²,

Wang³

2020

Synlett

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In spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of C–H functionalization chemistry and relative to key stoichiometric precedents. We then give an account of our group’s discovery and development of the catalytic α-functionalization of alkenes and alkynes with electrophilic reagents.Introduction Preliminary Stoichiometric WorkHydroxyalkylation Development and ScopeConclusions and Future Directions

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Palladium-Catalyzed Oxidative Allylic C−H Silylation

Cited by 72 publications

References 49 publications

Direct silylation reactions of inert C-H bonds via transition metal catalysis

Direct silylation reactions of inert C-H bonds via transition metal catalysis

Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

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