Cross-coupling reactions catalyzed by an N-heterocyclic carbene–Pd(<scp>ii</scp>) complex under aerobic and CuI-free conditions

Lu, Hongfei; Wang, Lin; Yang, Feifei; Wu, Runze; Shen, Wei

doi:10.1039/c4ra02480j

Cited by 27 publications

(11 citation statements)

References 36 publications

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“…However, Luo and Lu reported that that a Pd/IPr* catalyst ( 37 ) promotes selective Suzuki coupling of 18 at tosylate (Scheme 24 B). [65] This ligand was also used for a tosylate‐selective cross‐coupling of 18 with a terminal alkyne [66] …”

Section: Divergent Selectivity Between a Halide And A Pseudohalidementioning

confidence: 99%

Chemodivergence between Electrophiles in Cross‐Coupling Reactions

Reeves

Entz

Neufeldt

2021

Chemistry A European J

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Chemodivergent cross‐couplings are those in which either one of two (or more) potentially reactive functional groups can be made to react based on choice of conditions. In particular, this review focuses on cross‐couplings involving two different (pseudo)halides that can compete for the role of the electrophilic coupling partner. The discussion is primarily organized by pairs of electrophiles including chloride vs. triflate, bromide vs. triflate, chloride vs. tosylate, and halide vs. halide. Some common themes emerge regarding the origin of selectivity control. These include catalyst ligation state and solvent polarity or coordinating ability. However, in many cases, further systematic studies will be necessary to deconvolute the influences of metal identity, ligand, solvent, additives, nucleophilic coupling partner, and other factors on chemoselectivity.

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Section: Divergent Selectivity Between a Halide And A Pseudohalidementioning

confidence: 99%

Chemodivergence between Electrophiles in Cross‐Coupling Reactions

Reeves

Entz

Neufeldt

2021

Chemistry A European J

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“…44 Complex C44 proved to be an efficient catalyst for Sonogashira reaction of aryl bromides and some activated aryl chlorides under copper-and amine-free conditions (Table 5, entries 8-13).…”

Section: Sonogashira Cross Couplingmentioning

confidence: 99%

“…The complex C6 efficiently catalyzed the Heck reaction with low catalyst loading (1.0 mol%). 44 The catalytic reactions proceed under aerobic conditions and a variety of aryl bromides and terminal alkenes have been examined for their generality (Table 1, entries [23][24][25]. The complexes C7a-d, with a bidentate bis-NHC ligand having methyl and aryl substituents, showed catalytic activity in the Heck reaction of iodobenzene with styrene in DMA (Table 1, entry 26).…”

Section: Heck Reactionmentioning

confidence: 99%

“…Complex C6 efficiently catalyzed Sonogashira reactions of aryl bromides, aryl tosylates, and terminal alkynes under CuI-free condition with low catalyst loading (1.0 mol%) in the presence of air (Table 5, entries 1-7). 44 Complex C44 proved to be an efficient catalyst for Sonogashira reaction of aryl bromides and some activated aryl chlorides under copper-and amine-free conditions (Table 5, entries 8-13). 75 L-phenylalanine based C45 catalyzed the cross-coupling reaction of phenylacetylene with more reactive aryl iodides, with less reactive aryl bromides in the absence of copper co-catalysis, and the catalyst was not effective for aryl chloride (Table 5, entries 14-19).…”

Section: Sonogashira Cross Couplingmentioning

confidence: 99%

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Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Gürbüz¹,

Karaca²,

Özdemır³

et al. 2015

Turk J Chem

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This review is focused on new developments reported during the last 3 years concerning the catalytic performances of in situ formed or preformed NHC-Pd(II) complexes (NHC: N -heterocyclic carbene) for cross-coupling reactions such as Heck-Mizoraki (often shortened to the Heck reaction), Kumada, Negishi, Suzuki-Miyaura (often shortened to the Suzuki reaction), Sonogashira and Hiyama couplings, and the Buchwald-Hartwig aminations, which are extremely powerful in the formation of C-C and C-heteroatom bonds. Due to the great number of publications and limited space here, we made a special attempt to compile the relevant data in tables, which we hope will serve as a guide for chemists interested in these reactions. The syntheses of the precatalysts and the generally accepted reaction mechanisms are also briefly described.

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“…7 This catalyst system has been used by other groups, but it requires slow addition of alkyne to obtain a high product yield. Consequently, 1-dicyclohexylphosphino-2-(di- tert –butylphosphino-ethyl)ferrocene (CyPF- t Bu) has been used as the ligand in the palladium-catalyzed Sonogashira coupling of aryl tosylates, 8 and N -heterocyclic carbine-Pd(II) complexes have been reported by Lu and Shen 9 in the coupling of aryl tosylates.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates

Lee

Raja

et al. 2017

ACS Omega

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Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di- tert –butylphosphino-ethyl)ferrocene (CyPF- t Bu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.

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Cross-coupling reactions catalyzed by an N-heterocyclic carbene–Pd(ii) complex under aerobic and CuI-free conditions

Abstract: The catalytic reactions proceed with good yields with a low catalyst loading (1 mol%) under aerobic and CuI-free conditions for Sonogashira and Heck reactions.

Cited by 27 publications

References 36 publications

Chemodivergence between Electrophiles in Cross‐Coupling Reactions

Chemodivergence between Electrophiles in Cross‐Coupling Reactions

Cross coupling reactions catalyzed by (NHC)Pd(II) complexes

Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates

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