Suzuki–Miyaura Cross‐Coupling under Solvent‐Free Conditions

Asachenko, Andrey F.; Sorochkina, Kristina; Dzhevakov, Pavel B.; Topchiy, Maxim A.; Nechaev, Mikhail S.

doi:10.1002/adsc.201300741

Cited by 27 publications

(1 citation statement)

References 17 publications

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“…The carboxylic acids for the preparation of acid chlorides 1b – f , 1h , and 1a- d 5 were synthesized by the nickel-catalyzed Suzuki–Miyaura-type coupling of methyl 2-iodobenzoate with the corresponding arylboronic acids followed by hydrolysis with potassium hydroxide in aqueous ethanol . All of the 2-arylbenzoic acids (aryl = 4-MeC 6 H 4 , 4-FC 6 H 4 , 4-CF 3 C 6 H 4 , 4-MeOC 6 H 4 , 2-naphthyl, 3-MeC 6 H 4 , and C 6 D 5 ) are known. 4,4′-Dibromo-1,1′-biphenyl-2-carboxylic acid was prepared from 2,7-dibromofluorenone by the published procedure .…”

Section: Experimental Sectionmentioning

confidence: 99%

Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives

et al. 2014

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2-Arylbenzoyl chlorides undergo annulative coupling with internal alkynes in the presence of a catalyst system of [IrCl(cod)]2/P(t-Bu)3 to selectively afford the corresponding phenanthrene derivatives accompanied by elimination of carbon monoxide and hydrogen chloride. The reaction occurs without addition of any external base. Deuterium-labeling experiments using 2-(d5-phenyl)benzoyl chloride suggest that the rate-determining step does not involve the C2'-H bond cleavage. Formation of a [(t-Bu)3PH][(biphenyl-2,2'-diyl)Ir(CO)Cl2] complex dimer, of which the structure was determined by single-crystal X-ray analysis, from a stoichiometric reaction at 60 °C without addition of alkyne also supports the facile C-H cleavage.

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Section: Experimental Sectionmentioning

confidence: 99%

Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives

et al. 2014

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Miyaura Borylation and One‐Pot Two‐Step Homocoupling of Aryl Chlorides and Bromides under Solvent‐Free Conditions

et al. 2016

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Solvent‐free protocols for Miyaura borylation and the one‐pot, two‐step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one‐pot two‐step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.magnified image

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Highly reusable support‐free copper(II) complex of para‐hydroxy‐substituted salen: Novel, efficient and versatile catalyst for C─N bond forming reactions

Sharghi

Aberi

Shiri

2017

Applied Organom Chemis

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An air‐stable, highly active and versatile method for C─N bond forming reactions is reported. Under mild conditions using a highly reusable support‐free Cu(II)–salen complex, structurally diverse N‐aryl‐substituted compounds were obtained via direct C─N bond forming reaction of HN‐heterocycles with aryl iodides or three‐component C─N bond forming reaction of 2‐bromobenzaldehyde, aniline derivatives and sodium azide in good to excellent yields. C─N bond forming reaction for benzimidazole derivatives was also performed in the presence of the catalyst under ambient conditions. A series of hybrid benzimidazoles bearing morpholine, tetrazole and quinoxaline backbones were produced using this method. All reactions were performed in short times under air. The Cu(II) catalyst could be reused up to eight times in the direct cross‐coupling reaction of 9H–carbazole with iodobenzene without any decrease in its catalytic activity.

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Suzuki–Miyaura Cross‐Coupling under Solvent‐Free Conditions

Abstract: A solvent-free reaction protocol for Suzuki-Miyaura cross-couplings was developed.

Cited by 27 publications

References 17 publications

Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives

Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives

Miyaura Borylation and One‐Pot Two‐Step Homocoupling of Aryl Chlorides and Bromides under Solvent‐Free Conditions

Highly reusable support‐free copper(II) complex of para‐hydroxy‐substituted salen: Novel, efficient and versatile catalyst for C─N bond forming reactions

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