Phosphaadamantanes as Ligands for Palladium Catalyzed Cross-Coupling Chemistry:  Library Synthesis, Characterization, and Screening in the Suzuki Coupling of Alkyl Halides and Tosylates Containing β-Hydrogens with Boronic Acids and Alkylboranes

Brenstrum, Tim; Gerristma, David; Adjabeng, George M.; Frampton, Christopher S.; Britten, James F.; Robertson, Alan J.; McNulty, James; Capretta, Alfredo

doi:10.1021/jo048875+

Cited by 87 publications

(34 citation statements)

References 16 publications

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“…In other words, the mere fact that the solid catalyst can be recovered does not represent any advantage versus an extremely active homogeneous catalyst that can act at a much higher substrateto-palladium ratio, making its recovery for the reaction unnecessary. We note, however, that the substrate-to-palladium molar ratio used in this work is generally 0.4%, a value not uncommon for many homogeneous catalysts [5,61,62].…”

Section: Catalyst Recovery and Regenerationmentioning

confidence: 82%

Pd nanoparticles embedded in sponge-like porous silica as a Suzuki–Miyaura catalyst: Similarities and differences with homogeneous catalysts

Budroni

Corma

Garcı́a

et al. 2007

Journal of Catalysis

101

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Section: Catalyst Recovery and Regenerationmentioning

confidence: 82%

Pd nanoparticles embedded in sponge-like porous silica as a Suzuki–Miyaura catalyst: Similarities and differences with homogeneous catalysts

Budroni

Corma

Garcı́a

et al. 2007

Journal of Catalysis

101

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“…[18] Additionally, Capretta et al [19] successfully coupled secondary bromides with aryl boronic acids. In contrast to phosphine-ligated processes, the development of NHC-based protocols has been less successful.…”

mentioning

confidence: 99%

Easily Prepared Air‐ and Moisture‐Stable Pd–NHC (NHC=N‐Heterocyclic Carbene) Complexes: A Reliable, User‐Friendly, Highly Active Palladium Precatalyst for the Suzuki–Miyaura Reaction

O’Brien

Kantchev

Valente

et al. 2006

Chemistry A European J

776

441

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The synthesis of NHC-PdCl(2)-3-chloropyridine (NHC=N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.

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“…[77] A very similar reaction using a phospha-adamantane ligand and dioxane as solvent for the coupling of n-butylboronic acid with n-bromododecene was reported by Capretta. [78] Under these reaction conditions, the expected product was obtained in 54 % yield (Scheme 55).…”

Section: Couplings Of Alkyl Halide Derivatives With Alkylboronic Acidmentioning

confidence: 97%

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

2008

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Palladium‐catalysed Suzuki–Miyaura cross‐couplings of organoboronic acids or organotrifluoroborates with aryl and alkenyl halides or triflates have become classic methods for generating carbon–carbon bonds. For this reaction, not only sp2‐hybridized but also sp3‐hybridized organoboron derivatives can be employed. However, alkylboronic acids or trifluoroborates are generally less reactive than arylboron derivatives. The coupling of primary alkylboronic acids or alkyltrifluoroborates with aryl or alkenyl halides is well known, and the reaction gives the coupling products with high selectivities, relatively high turnover numbers and in good yields with several catalysts. On the other hand, secondary alkylboronic acids or trifluoroborates, except for cyclopropylboron derivatives, are much less reactive, and very few catalyst are able to activate such compounds. Because of the hybridization of cyclopropanes, which confers significant aromatic character, several reactions have successfully been performed with cyclopropylboronic acids or trifluoroborates. The stereochemistries of substituted cyclopropylboron derivatives were maintained in the course of the reactions. For all these couplings with primary or secondary alkylboron derivatives, aryl iodides, bromides, chlorides or triflates and alkenyl iodides, bromides or triflates were employed. Alkenyl chlorides have attracted less attention. The reactions with alkenyl halides are stereoselective. A few examples of couplings between sp3‐hybridized organoboronic acids and alkyl halides have also been reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Phosphaadamantanes as Ligands for Palladium Catalyzed Cross-Coupling Chemistry: Library Synthesis, Characterization, and Screening in the Suzuki Coupling of Alkyl Halides and Tosylates Containing β-Hydrogens with Boronic Acids and Alkylboranes

Cited by 87 publications

References 16 publications

Pd nanoparticles embedded in sponge-like porous silica as a Suzuki–Miyaura catalyst: Similarities and differences with homogeneous catalysts

Pd nanoparticles embedded in sponge-like porous silica as a Suzuki–Miyaura catalyst: Similarities and differences with homogeneous catalysts

Easily Prepared Air‐ and Moisture‐Stable Pd–NHC (NHC=N‐Heterocyclic Carbene) Complexes: A Reliable, User‐Friendly, Highly Active Palladium Precatalyst for the Suzuki–Miyaura Reaction

Suzuki–Miyaura Cross‐Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates

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