Palladium-Catalyzed Cross-Coupling Reaction of Secondary Benzylic Bromides with Grignard Reagents

López-Pérez, Ana; Adrio, Javier; Carretero, Juan C.

doi:10.1021/ol902335c

Cited by 117 publications

(41 citation statements)

References 52 publications

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“…In 2009, Adrio and Carretero discovered that Grignard reagents were successful coupling partners for the same electrophile, such that the reaction of benzhydryl bromide with 4-fluorophenyl-magnesium bromide gave the corresponding triarylmethane in excellent yield employing a combination of Pd(MeCN) 2 Cl 2 and Xantphos as the catalyst (Scheme 1b). 12 In 2008, the Kuwano group reported that diarylmethyl methyl carbonate was a good alternative to diarylmethyl halides as the electrophile for the production of triarylmethanes (Scheme 2). 13 The carbonate derivatives were reacted with arylboronic acids in the presence of a catalytic amount of [Pd(ally)Cl] 2 with bidentate 1,5-bis(diphenylphosphino)-pentane (DPPPent) ligand and K 2 CO 3 as the base.…”

Section: Synthesis Of Achiral Triarylmethanes Bymentioning

confidence: 99%

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

2015

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Triarylmethanes and related compounds are fascinating molecules because of their structural and physical properties, many potential applications in organic functional materials, and high biological activity. Recently, catalysis has provided new synthesis routes to triarylmethanes with high selectivity and diversity, including the possibility of preparing enantiomerically enriched derivatives, which is typically challenging using classical methods. This Perspective reviews recent advances in new synthesis approaches to triarylmethanes using well-defined transition metal catalysts. These methods will allow the development of new, unexplored triarylmethane structures.

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Section: Synthesis Of Achiral Triarylmethanes Bymentioning

confidence: 99%

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

2015

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“…In many cases, no impact of the purity of the iron source on the catalytic activity was observed [106]. Also, it seems that the Kumadatype cross coupling of Grignard reagents and halides, further discussed by Robin Bedford in [29], is not due to metal contaminants; palladium-catalyzed Kumada reactions appear not to work ligand-free [107][108][109]. The lower efficiency of palladium-catalyzed Kumada-type couplings was attributed to the high reactivity of Grignard reagents compared to the nucleophiles typically employed in crosscoupling chemistry, such as boranes [109].…”

Section: Enantioselective Iron Catalysis and Stoichiometric Consideramentioning

confidence: 99%

Iron Catalysis: Historic Overview and Current Trends

Bauer

2015

Topics in Organometallic Chemistry

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Iron catalysis is a growing area of research, as seen by an exponential increase in the publication activities on the topic. This introductory chapter provides a historic overview of the development of iron catalysis including some notable milestones. The advantages of iron, i.e., its abundance, low price, and relative nontoxicity, are discussed, and an overview of the main type of reactions catalyzed by iron is outlined. The advances of heterogeneous iron catalysis (which is not covered in this volume) are exemplified with a few notable cases. Finally, the potential impact of metal impurities in iron sources on the catalytic activity is discussed.

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“…4-(1-Phenylethyl)anisole (2u): [43] Eluent: hexane/ethyl acetate = 20/1; colorless liquid; yield: 0.148 g (70%). …”

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confidence: 99%

Extremely Efficient Cross‐Coupling of Benzylic Halides with Aryltitanium Tris(isopropoxide) Catalyzed by Low Loadings of a Simple Palladium(II) Acetate/Tris(p‐tolyl)phosphine System

et al. 2010

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Highly efficient coupling reactions of benzylic bromides or chlorides with aryltitanium tris(isopropoxide) [ArTi(O-i-Pr)(3)] catalyzed by a simple palladium(II) acetate/tris(p-tolyl)phosphine [Pd(OAc)(2)/P(p-tolyl)(3)] system are reported. The coupling reactions proceed in general at room temperature employing low catalyst loadings of 0.02 to 0.2 mol%, affording coupling products in excellent yields of up to 99%. For benzylic bromides bearing strong electron-withdrawing cyano (CN) or trifluoromethyl (CF(3)) substituents, the reactions require a higher catalyst loading of 1 mol%, or the reactions are carried out at 60 degrees C. The catalytic system also tolerates (1-bromoethyl)benzene bearing beta-hydrogen atoms while using a catalyst loading of 1 mol% to afford the coupling product in a 70% yield

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Palladium-Catalyzed Cross-Coupling Reaction of Secondary Benzylic Bromides with Grignard Reagents

Cited by 117 publications

References 52 publications

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

Iron Catalysis: Historic Overview and Current Trends

Extremely Efficient Cross‐Coupling of Benzylic Halides with Aryltitanium Tris(isopropoxide) Catalyzed by Low Loadings of a Simple Palladium(II) Acetate/Tris(p‐tolyl)phosphine System

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