Ruthenium-Catalyzed <i>Ortho</i>-Alkenylation of Aromatic Ketones with Alkenes by C–H Bond Activation

Padala, Kishor; Jeganmohan, Masilamani

doi:10.1021/ol202580e

Cited by 248 publications

(66 citation statements)

References 85 publications

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“…35 When a cationic rhodium catalyst [Cp*Rh(CH 3 CN) 3 ](SbF 6 ) 2 was used with stoichiometric silver acetate, Li and coworkers discovered aromatic ketones and enones underwent a C-H alkylation/aldol condensation sequence instead of an oxidative olefination reaction (Scheme 15). 35 When a cationic rhodium catalyst [Cp*Rh(CH 3 CN) 3 ](SbF 6 ) 2 was used with stoichiometric silver acetate, Li and coworkers discovered aromatic ketones and enones underwent a C-H alkylation/aldol condensation sequence instead of an oxidative olefination reaction (Scheme 15).…”

Section: View Article Onlinementioning

confidence: 99%

Transition metal-catalyzed ketone-directed or mediated C–H functionalization

et al. 2015

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Transition metal-catalyzed C-H functionalization has evolved into a prominent and indispensable tool in organic synthesis. While nitrogen, phosphorus and sulfur-based functional groups (FGs) are widely employed as effective directing groups (DGs) to control the site-selectivity of C-H activation, the use of common FGs (e.g. ketone, alcohol and amine) as DGs has been continuously pursued. Ketones are an especially attractive choice of DGs and substrates due to their prevalence in various molecules and versatile reactivity as synthetic intermediates. Over the last two decades, transition metal-catalyzed C-H functionalization that is directed or mediated by ketones has experienced vigorous growth. This review summarizes these advancements into three major categories: use of ketone carbonyls as DGs, direct β-functionalization, and α-alkylation/alkenylation with unactivated olefins and alkynes. Each of these subsections is discussed from the perspective of strategic design and reaction discovery.

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Section: View Article Onlinementioning

confidence: 99%

Transition metal-catalyzed ketone-directed or mediated C–H functionalization

et al. 2015

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“…The use of AgSbF 6 as an additive to Ru II was introduced by Jeganmohan. [30] The use of costly additives such as AgSbF 6 makes the reaction environmentally hostile and also increases the number of byproducts, which thereby decreases the yield.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Free Ruthenium(II)‐Catalyzed C–H Activation: Synthesis of Alkenylarylpyrazole Derivatives

Shome

Singh

2015

Eur J Org Chem

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Keywords: C-H activation / Ruthenium / Alkenylation / Nitrogen heterocyclesThe Ru II carboxylate complex Ru(MesCO 2 ) 2 (p-cymene) (Mes = mesityl) was found to be an efficient catalyst for the direct dehydrogenative alkenylation of N-arylpyrazoles by using styrenes and acrylates in the presence of Cu(OAc) 2 ·H 2 O in open air. The highly step-economical C-H bond functionalization process is characterized by a wide substrate scope and significant chemoselectivity, which allowed direct alkenylation to be performed either under solvent-free reaction con-

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“…Likewise, in 2011, Padala and Jeganmohan [69] reported an oxidative Ru-catalyzed-directed arylation of activated olefins. The Heck-Mizoroki products were obtained in very good yields (Figure 4.35).…”

Section: C(sp 2 )-H Activations 207mentioning

confidence: 98%

“…35 A cross-section of results for the Ru-catalyzed ortho-alkenylation of aromatic ketones as described by Padala and Jeganmohan[69].…”

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confidence: 99%

C–H Bond Activation for Arylations

2014

Catalytic Arylation Methods

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Ruthenium-Catalyzed Ortho-Alkenylation of Aromatic Ketones with Alkenes by C–H Bond Activation

Abstract: A ruthenium-catalyzed chelation-assisted C-H bond activation of aromatic ketones and the reaction with olefins to provide Heck-type products in good to excellent yields with a high regio- and stereoselective manner is described.

Cited by 248 publications

References 85 publications

Transition metal-catalyzed ketone-directed or mediated C–H functionalization

Transition metal-catalyzed ketone-directed or mediated C–H functionalization

Solvent‐Free Ruthenium(II)‐Catalyzed C–H Activation: Synthesis of Alkenylarylpyrazole Derivatives

C–H Bond Activation for Arylations

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