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2 article(s) from Nishikata, Takashi

Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

Goki Hirata,
Yu Yamane,
Naoya Tsubaki,
Reina Hara and
Takashi Nishikata

Beilstein J. Org. Chem. 2020, 16, 502–508, doi:10.3762/bjoc.16.45

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Scheme 1: Reaction modes of alkyne.

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Figure 1: Substrate scope of 1 and 2. ^aConducted at 80 °C for 24 h in MeCN with CuBr (10 mol %), 1,10-Phen (2...

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Scheme 2: Proposed mechanism.

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Scheme 3: Control experiment.

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Scheme 4: Reaction of 2a and 4a.

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Figure 2: Substrate scope of 2 and 4. ^aConducted at 100 °C for 20 h in 1,4-dioxane with CuI (10 mol %), 1,10-...

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Letter

Published 26 Mar 2020

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Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

Takashi Nishikata,
Alexander R. Abela,
Shenlin Huang and
Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

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Figure 1: Road map to enhanced C–H activation reactivity.

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Scheme 1: Concerted metalation–deprotonation and elelectrophilic palladation pathways for C–H activation.

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Scheme 2: Routes for generation of cationic palladium(II) species.

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Scheme 3: Optimized conditions for C–H arylations at room temperature.

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Scheme 4: Biaryl formation catalyzed by Pd(OAc)₂.

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Figure 2: C–H arylation results. Conditions A: Conducted at rt for 20 h in 2 wt % Brij 35/water (1 mL) with 1...

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Figure 3: Monoarylations in water at rt. Conditions A: Conducted at rt for 20 h in 2 wt % Brij 35/water with ...

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Scheme 5: Selective arylation of a 1-naphthylurea derivative.

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Figure 4: Fujiwara–Moritani coupling rreactions in water. Conditions A: 10 mol % [Pd(MeCN)₄](BF₄)₂, 1 equiv B...

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Figure 5: Optimization. Conducted at rt for 8 h or as otherwise noted in EtOAc with 10 mol % Pd catalyst, AgO...

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Figure 6: Representative results in EtOAc. Conducted at rt in EtOAc with 10 mol % Pd(OAc)₂, HBF₄ (1 equiv), a...

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Scheme 6: Previous syntheses of boscalid^®.

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Scheme 7: Synthesis of boscalid^®. ^aConducted at rt for 20 h in EtOAc with 10 mol % [Pd(MeCN)₄](BF₄)₂, BQ (5 e...

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Scheme 8: Hypothetical reaction sequence for cationic Pd(II)-catalyzed aromatic C–H activation reactions.

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Scheme 9: Palladacycle formation.

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Figure 7: X-ray structure of palladacycle 6 with thermal ellipsoids at the 50% probability level. BF₄ and hyd...

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Figure 8: NMR studies. A: The reaction of [Pd(MeCN)₄](BF₄)₂ and 3-MeOC₆H₄NHCONMe₂ in acetone-d₆. B: The react...

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Scheme 10: The generation of cationic Pd(II) from Pd(OAc)₂.

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Scheme 11: Electrophilic substitution of aromatic hydrogen by cationic palladium(II) species.

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Scheme 12: Attempted reactions of palladacycle 6.

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Scheme 13: The impact of MeCN on C-H activation/coupling reactions.

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Scheme 14: Stoichiometric MeCN-free reactions. ^a2% Brij 35 was used instead of EtOAc.

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Scheme 15: The reactions of divalent palladacycles.

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Scheme 16: Role of BQ in stoichiometric Fujiwara–Moritani and Suzuki–Miyaura coupling reactions. ^aYields based...

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Scheme 17: Proposed role of BQ in Fujiwara–Moritani reactions.

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Scheme 18: Proposed role of BQ in Suzuki–Miyaura coupling reactions.

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Scheme 19: Stoichiometric C–H arylation of iodobenzene. ^aYields based on Pd.

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Scheme 20: Impact of acetate on the cationicity of Pd.

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Scheme 21: Roles of additives in C–H arylation.

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Scheme 22: Cross-coupling in the presence of AgBF₄.

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Scheme 23: A proposed catalytic cycle for Fujiwara–Moritani reactions.

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Scheme 24: Proposed catalytic cycle of C–H activation/Suzuki–Miyaura coupling reactions.

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Scheme 25: A proposed catalytic cycle for C–H arylation involving a Pd(IV) intermediate.

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Scheme 26: Selected reactions of divalent palladacycles.

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Full Research Paper

Published 20 May 2016

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