Palladium Nanoparticle Catalyzed Hiyama Coupling Reaction of Benzyl Halides

Srimani, Dipankar; Bej, Ansuman; Sarkar, Amitabha

doi:10.1021/jo1003373

Cited by 92 publications

(43 citation statements)

References 99 publications

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“…To further demonstrate the utility of this protocol, we synthesized, without the aid of ag love box, ap recursor to naturally occurring 2,4-bis(4-hydroxybenzyl)phenol (12; Scheme 3). [42] Compound 12 was recently reported to be an inhibitor of heat shock transcription factor 1and enhance the effectiveness of conventional anticancer agents (e.g.,cisplatin and paclitaxel). [43] Di(p-anisole)zinc was generated in situ by lithium/halogen exchange of 4-bromoanisole with nBuLi in anhydrous diethyl ether followed by zincation with ZnCl 2 .…”

Section: Methodsmentioning

confidence: 99%

Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

2015

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The direct C(sp 2 ) À C(sp 3 )c ross-coupling of diaryl zinc reagents with benzylic,p rimary,s econdary,a nd tertiary alkylhalides proceeded in the absence of coordinating ethereal solvents at ambient temperature without the addition of acatalyst. The C(sp 2 )ÀC(sp 3 )cross-coupling showed excellent functional-group tolerance,and products were isolated in high yields,g enerally without the requirement for purification by chromatography.This process represents an expedient, operationally simple method for the construction of new C(sp 2 )À C(sp 3 )b onds.

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Section: Methodsmentioning

confidence: 99%

Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

2015

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“…Benzyl and allyl halides were coupled with aryltrialkoxysiloxanes by the same group in 2010 using PEG-600-stabilized Pd-NPs. A tentative mechanism was proposed for the "nano"-Hiyama coupling as shown in Figure 5.8, 99 in which oxidative addition of the allyl halides occurs on the surface of the particles.…”

Section: Hiyama Couplingmentioning

confidence: 99%

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Banerjee

Scott

2013

Nanocatalysis Synthesis and Applications

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INTRODUCTIONIn the last century, the synthetic organic chemist had formidable resources available for the design and preparation of new complex molecules. 1, 2 However, in the twenty-first century, it is essential for a successful synthetic strategy not only to yield new, pure products selectively but also to develop processes that are environmentally friendly, cost-effective, and dependent on renewable feedstocks rather than on fast-depleting fossil fuels or their derivatives. [3][4][5] The burgeoning field of catalytic nanomaterials, or nanocatalysts, offers an opportunity to the modern synthetic chemist to follow the tenets of green chemistry without compromising on crucial factors such as yield and selectivity of products. 6 Current emphasis on catalysis using nanomaterials, which straddles the boundaries of homogeneous and heterogeneous catalysis, often combining the benefits of both, underscores the quest for recyclable catalytic materials. 7 In this field of research, the formation of new C C bonds using nanomaterials has emerged as a challenging new problem that is being studied across the globe. 8 C C couplings are now a staple of modern organic chemistry, as evidenced by the recent Nobel Prize award in chemistry to Heck, Negishi, and Suzuki in 2010. A recent Web of Knowledge R search shows the almost exponential growth in the number of literature reports related to interdisciplinary research involving nanochemistry and organic synthesis during the past decade ( Figure 5.1).

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“…The products 3a, [19] 3b, [21] 3c, [19] 3d, [36] 3e, [36] 3f, [21] 3g, [37] 3h, [7] 3i [38] and 3j [19] were characterized by comparing their 1 H NMR and 13 C NMR spectra with those mentioned in the references. …”

Section: General Procedures For Palladacycle-catalyzed Suzuki Cross-comentioning

confidence: 99%

Cyclopalladated ferrocenylimine as an efficient catalyst for the syntheses of diarylmethane derivatives

Peng

et al. 2012

Applied Organom Chemis

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The cyclopalladated ferrocenylimine adducts Ia-c were evaluated in the Suzuki cross-coupling reaction of benzyl halides with arylboronic acids. The tricyclohexylphosphine adduct Ia exhibited highly catalytic activity for the coupling of aryl and heteroaryl boronic acids containing various functional groups with benzylic bromides and chlorides (up to 99% yield), furnishing diarylmethane derivatives with low catalyst loading (1 mol%). It is worth noting that catalyst Ia can be reused eight times without losing its catalytic activity.

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Palladium Nanoparticle Catalyzed Hiyama Coupling Reaction of Benzyl Halides

Cited by 92 publications

References 99 publications

Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Cyclopalladated ferrocenylimine as an efficient catalyst for the syntheses of diarylmethane derivatives

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Palladium Nanoparticle Catalyzed Hiyama Coupling Reaction of Benzyl Halides

Cited by 92 publications

References 99 publications

Direct C(sp2)C(sp3) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Direct C(sp2)C(sp3) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Cyclopalladated ferrocenylimine as an efficient catalyst for the syntheses of diarylmethane derivatives

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Product

Resources

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Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides

Direct C(sp²)C(sp³) Cross‐Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides