Palladium-catalyzed multiple arylation of phenyl ketones with aryl bromides

Satoh, Tetsuya; Kametani, Yoko; Terao, Yoshito; Miura, Masahiro; Nomura, Masakatsu

doi:10.1016/s0040-4039(99)00973-9

Cited by 123 publications

(39 citation statements)

References 13 publications

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“…In pioneering studies, Miura and co-workers developed methods for the direct arylation of aromatic carbonyl compounds, such as ketones, amides, or aldehydes, with aryl bromides or triflates used as the electrophiles (Scheme 58). [108,109] More recently, Sanford and co-workers investigated the use of iodonium salts, such as [Ph 2 I][BF 4 ] (153), for the direct arylation of 2-aryl pyridines (Scheme 59). [27] Here, detailed mechanistic studies indicated that a palladium(II)/palladium(IV) catalytic cycle [110][111][112] was operative rather than a palladium(0)/palladium(II) cycle, which had generally been proposed for direct arylations with aryl (pseudo)halides as electrophiles.…”

Section: Aryl Triflates Iodides Bromides and Their Derivativesmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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The area of transition-metal-catalyzed direct arylation through cleavage of C-H bonds has undergone rapid development in recent years, and is becoming an increasingly viable alternative to traditional cross-coupling reactions with organometallic reagents. In particular, palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations. Furthermore, less expensive copper, iron, and nickel complexes were recently shown to be effective for economically attractive direct arylations.

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Section: Aryl Triflates Iodides Bromides and Their Derivativesmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

2009

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“…Recently, versatile palladium-catalyzed a-arylations of ketone enolates [8] have been developed elegantly by Buchwald, [9] Hartwig, [10] and Miura [11] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Progress in the Palladium-Catalyzed α-Arylation of Ketones with Chloroarenes

Ehrentraut

Zapf

Beller

2002

Advanced Synthesis & Catalyis

174

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“…The groups of Miura and Murai pioneered research on direct arylation protocols initially focusing on palladium catalysis, [18][19] and later extending to ruthenium. 20 Already in 1996…”

Section: Investigations Of C(sp 2 )-H Activationmentioning

confidence: 99%

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

Schnürch¹

2015

Arkivoc

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This account summarizes our work in the field of direct C-H bond functionalization. We have explored methods in the area of directing group assisted C(sp 2 )-H and C(sp 3 )-H activation and investigated arylation as well as deuteration reactions. In these transformations either ruthenium or palladium catalysts were applied. In case of C(sp 2 )-H activation, we developed a protocol for the synthesis of ortho arylated anilines and disclosed the first method for a direct arylation in a continuous flow reactor. Additionally, we applied a direct arylation in the synthesis of compounds which can accelerate cell differentiation. In the field of C(sp 3 )-H activation we developed a protocol for the selective mono-arylation of piperidine and three different arylation protocols for acyclic amines employing either aryl chlorides, aryl bromides, aryl iodides, or arylboronic acid esters as the aryl donor.

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Palladium-catalyzed multiple arylation of phenyl ketones with aryl bromides

Cited by 123 publications

References 13 publications

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Transition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage

Progress in the Palladium-Catalyzed α-Arylation of Ketones with Chloroarenes

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

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