An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides

Broekemier, Noland William; Broekemier, Noah Curtis; Short, Randall T.; Palencia, Hector

doi:10.5155/eurjchem.5.1.162-166.940

Cited by 3 publications

(2 citation statements)

References 33 publications

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“…89,90 In 2014, Palencia and coworkers described a well-defined unsymmetrical N-heterocyclic carbene-palladium-η 3 -allyl chloride complex 224 that promoted the cross-coupling of aryl bromides and activated aryl chlorides 222 with boronic acids 221 under moderate conditions (Scheme 65). 91…”

Section: Scheme 64 Activation Of -Allylpalladium Precatalystsmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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This review aims to summarize the development of the chemistry of π-allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates.1 Introduction2 π-Allylpalladium Complexes Generated from Allyl Electrophiles2.1 Activated Allylic Compounds2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons2.3 Total Syntheses3 π-Allylpalladium Complexes Generated from Dienes3.1 Conjugated Dienes3.2 Allenes4 π-Allylpalladium Complexes Exploited as Reactants and Precatalysts4.1 Allylpalladium-Catalyzed Dehydrogenation4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters4.3 Allylpalladium-Based Precatalysts5 Conclusions

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Section: Scheme 64 Activation Of -Allylpalladium Precatalystsmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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“…We are interested in the chemistry of NHCs [37,38] and sought to develop a protocol to catalyze the benzoin condensation with NHCs, using the minimum amount of solvent and a catalytic amount of 5 mol%. Our previous experience with the transesterification of glycerol and dimethyl carbonate, catalyzed by NHCs under mild conditions in short time, encouraged us to evaluate some of our previously used catalysts, and others, to explore their catalytic efficiency on the benzoin condensation.…”

Section: Introductionmentioning

confidence: 99%

Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions

et al. 2019

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The benzoin condensation was used to evaluate the catalytic activity of different N-heterocyclic carbenes as a function of their structure and N-substituents. There is a correlation between the length of an N-alkyl substituent and its performance as an organocatalyst. Heteroaromatic aldehydes were found to be the most reactive, among the screened substrates, finishing the reaction in 30 minutes, with almost quantitative yields. On the other hand, p-nitrobenzaldehyde, a strongly electrophilic aldehyde, was the least reactive. Electronic effects have little influence on the reaction yield but steric effects can dramatically reduce it. The preformed organocatalyst reacts faster than the generated in situ, with minimum solvent.

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