"Greening Up" the Suzuki Reaction

Aktoudianakis, Evangelos; Chan, Elton; Edward, Amanda R.; Jarosz, Isabel; Lee, Vicki; Mui, Leo; Thatipamala, Sonya S.; Dicks, Andrew P.

doi:10.1021/ed085p555

Cited by 53 publications

(29 citation statements)

References 10 publications

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“…[12] Effort was put in to find cost-effective ands ustainable protocols for their synthesis. [13] Thus,v arious Lewis acids such as Cp 2 Zr 2 Cl 2 , [14] CeCl 3 ·7H 2 O, [15] SbCl 3 , [16] SnCl 2 ·2H 2 O, [17] ZnCl 2 , [18] RuCl 3 , [19] AlCl 3 ·6H 2 O, [20] and FeCl 3 / Si(OEt) 4 [21] were employed to catalyze their formation. Despite the advances,f acing us are problems such as long reactiont ime, large catalyst loading,l ow yield, toxicity,h arsh reactionc onditions andc omplicated procedure.N ot long ago,w er eported that zirconocene bis(perfluoro-butanesulfonate) shows high catalytic efficiency for the synthesis of N-heterocyclic compounds.…”

Section: Resultsmentioning

confidence: 99%

Air‐stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N‐Containing Compounds

Wang

et al. 2016

Adv Synth Catal

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Tr iphenyl bismuth bisperfluorooctanesulfonate is an air-a nd water-stable Lewis acid. It exhibits high catalytic efficiency for the synthesis of nitrogen heterocycles such as diindolylmethane derivatives, dihydropyrimidinones,d ihydropyridinesa nd 1,2-disubstitued benzimidazoles under mild condition. Furthermore,i tc an be reused without loss of activity in at est of five cycles.This catalytic systema ffords asimple and efficient wayfor the synthesisofN -containing compounds.

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Section: Resultsmentioning

confidence: 99%

Air‐stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N‐Containing Compounds

Wang

et al. 2016

Adv Synth Catal

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“…There have been multiple Suzuki-type reactions published for the undergraduate laboratory curriculum employing both aryl bromides (21)(22)(23) and aryl iodides (24) as coupling agents with arylboronic acids using various palladium catalysts.…”

Section: Suzuki-miyaura Coupling Reaction Of 5iodovanillinmentioning

confidence: 99%

“…The procedure that appeared most compatible with 5iodovanillin was that of Dicks and co-authors (24), who demonstrated that phenylboronic acid can be crosscoupled with 4-iodophenol using 10% Pd/C, K 2 CO 3 , in refluxing water for 30 min. This experiment featured ligand-free use of a palladium source, water as a solvent, and facile isolation of the product.…”

Section: Suzuki-miyaura Coupling Reaction Of 5iodovanillinmentioning

confidence: 99%

Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles

Palesch

Gilles

Chycota

et al. 2019

Green Chemistry Letters and Reviews

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A two-step synthetic sequence was developed for the undergraduate organic chemistry laboratory using vanillin as the starting material. The multi-step synthesis was designed to replace two traditional experiments teaching electrophilic aromatic substitution and carbon-carbon bond forming chemistries with greener transformations. Vanillin is iodinated using Oxone® and potassium iodide in refluxing water, and students are tasked with determining the position of aromatic substitution using 1 H NMR spectroscopy. The tan, shiny, pleasant-smelling iodovanillin is subsequently used in an aqueous Suzuki-Miyaura reaction with para-methylphenylboronic acid; strategically chosen to afford a second instructive 1 H NMR spectrum. Both conventional heating and microwave conditions can be employed for the palladium-catalyzed reaction. This synthetic sequence, successfully performed over multiple semesters by hundreds of students, models green chemistry principles through the use of a potentially renewable feedstock and safer reagents, the choice of water as a safer reaction solvent, and the employment of a catalytic reaction. Additionally, the sequence minimizes waste in teaching labs through use of an intermediate product.

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“…Research indicates many such reactions are possible in pure water (36). A Suzuki cross-coupling reaction was designed to synthesize 4-phenylphenol, a biaryl component of important non-steroidal antiinflammatory drugs (NSAIDs) (37). This approach employs water as the sole reaction solvent, features inexpensive palladium on carbon as the active catalyst and solid purification by recrystallization from aqueous methanol (Scheme 10).…”

Section: Transition Metal-catalyzed Reactionsmentioning

confidence: 99%

A review of aqueous organic reactions for the undergraduate teaching laboratory

Dicks

2009

Green Chemistry Letters and Reviews

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This article summarizes the wide scope of aqueous organic reactivity from a pedagogical perspective. It is aimed at university instructors with the goal of promoting water as a solvent in academic institutions. Recently, extensive industrial and scholarly research has concerned development of organic reactions in aqueous media. Many examples are now possible in the student laboratory including carbonÁcarbon/carbonÁnitrogen bondforming reactions and functional group transformations (e.g. oxidations, reductions, and halohydrations). Experiments are summarized from the educational literature (journal articles and laboratory textbooks) and their green features are described. Using water as solvent often promotes significant rate enhancements and operational simplicity Á both of importance when training undergraduates during limited laboratory time. Environmental benefits of using water are additionally highlighted to students' first hand in relation to the Twelve Principles of Green Chemistry.

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"Greening Up" the Suzuki Reaction

Cited by 53 publications

References 10 publications

Air‐stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N‐Containing Compounds

Air‐stable Organobismuth(V) Bisperfluorooctanesulfonate as an Efficient Catalyst for the Synthesis of N‐Containing Compounds

Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles

A review of aqueous organic reactions for the undergraduate teaching laboratory

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