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2 article(s) from Bardin, Vadim V

Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles

Anton Yu. Shabalin,
Nicolay Yu. Adonin and
Vadim V. Bardin

Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69

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Scheme 1: Preparation of polyfluoroorganotrifluoroborates.

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Scheme 2: Interaction of K[C₆F₅BF₃] (1-K) with methyllithium (byproducts of hydrodeboration are not depicted)....

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Scheme 3: Interaction of M[C₆F₅BF₃] (1-M) with butyllithium (byproducts of hydrodeboration are not depicted).

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Scheme 4: Interaction of K[C₆F₅BF₃] (1-K) with phenyllithium (byproducts of hydrodeboration are not depicted)....

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Scheme 5: Hydrodeboration of 6-K, 7-K, 8-K and 9-K in MeOH.

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Scheme 6: Hydrodeboration of 1-K, 10-K and 11-K in methyl cellosolve.

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Scheme 7: Hydrodeboration of 10-K, 11-K, 12-K and 13-K in MeOH.

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Scheme 8: Preparation of 1-Li and 1-N.

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Scheme 9: Formation of 2-R-tetrafluorophenyltrifluoroborates.

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Scheme 10: Interaction between C₆F₅BF₃⁻ and PhLi.

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Scheme 11: Interaction of 1-K with MeONa.

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Scheme 12: Interaction of M[RC₆F₅BF₃] with lithium halides.

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Scheme 13: Assumed role of lithium halides.

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Published 12 Apr 2017

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Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki–Miyaura reactions: relative reactivity of K[4-RC₆F₄BF₃] and the role of silver-assistance in acceleration of transmetallation

Vadim V. Bardin,
Anton Yu. Shabalin and
Nicolay Yu. Adonin

Beilstein J. Org. Chem. 2015, 11, 608–616, doi:10.3762/bjoc.11.68

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Scheme 1: The assumed silver(I) oxide assisted transmetallation with organoboronic acids.

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Scheme 2: Cross-coupling of K[4-RC₆F₄BF₃] (1a–r) with 3-IC₆H₄F (2) and 4-IC₆H₄F (3).

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Scheme 3: Attempted synthesis of 7 (3’-F) and 8 (4’-F) by cross-coupling reaction.

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Scheme 4: Synthesis of biphenyls 10a,c–f,h–p.

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Scheme 5: Pd-catalyzed cross-coupling of 1a and salts 1b–p (1:1) with 11 (the results are presented in Table 3 and o...

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Scheme 6: The cross-coupling of 1a with 11 in the presence of different silver(I) compounds.

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Scheme 7: General concept of Pd-catalyzed Suzuki–Miyaura reaction.

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Scheme 8: Assumed silver(I)-assisted transmetallation of weakly nucleophilic aryitrifluoroborates.

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Published 04 May 2015

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Substitution of fluorine in M[C6F5BF3] with organolithium compounds: distinctions between O- and N-nucleophiles

Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki–Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation

Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles

Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki–Miyaura reactions: relative reactivity of K[4-RC₆F₄BF₃] and the role of silver-assistance in acceleration of transmetallation