A novel green protocol for ligand free Suzuki–Miyaura cross-coupling reactions in WEB at room temperature

Boruah, Preeti Rekha; Ali, Abdul Aziz; Saikia, Bishwajit; Sarma, Diganta

doi:10.1039/c4gc02522a

Cited by 139 publications

(56 citation statements)

References 38 publications

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“…Green procedure of coupling reaction is booming, and a lot of ligand‐free or green solvent coupling reactions are rapidly developing. Recently, some chemists such as Basu, Liu, Bora, Liu, Schatz, Sarma, Handa (Scheme B) reported a series of ligand‐free Suzuki–Miyaura coupling reaction to yield the biaryl products. Since the first research reported by Genêt group in 1997, potassium aryltrifluoroborates were widely used as an alternative to organoboronic acid in Suzuki–Miyaura coupling reaction recently .…”

Section: Introductionmentioning

confidence: 99%

Water Phase, Room Temperature, Ligand‐Free Suzuki–Miyaura Cross‐Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage

Zhang

Wang

Tang³

et al. 2020

Eur J Org Chem

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We report herein a green strategy for synthesis of aryl ketones from twisted amides by using Pd(OAc)2 as catalysts. This method shows high functional group tolerance to offer a variety of ketones in good yields under mild conditions (up to 94 %). Notably, this methodology demonstrates the first water phase, room temperature, ligand‐free Suzuki–Miyaura coupling through C–N bond cleavage, which is environmentally friendly and might facilitate the development of amide based green chemistry.

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Section: Introductionmentioning

confidence: 99%

Water Phase, Room Temperature, Ligand‐Free Suzuki–Miyaura Cross‐Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage

Zhang

Wang

Tang³

et al. 2020

Eur J Org Chem

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show abstract

“…Although recently some efficient methodologies have been developed for SMC by avoiding external base and ligands, there is still a demand to develop new synthetic protocols since unexpected results can be seen in SMC by a small change of reaction conditions like temperature, ligand, base, nature of substrates, solvent, etc . Typical trends in substrate selectivity and reactivity may be broken .…”

Section: Introductionmentioning

confidence: 99%

Palladium‐catalysed room‐temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio‐derived sustainable and renewable medium

Appa

Prasad

Lakshmidevi

et al. 2019

Applied Organom Chemis

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An agro waste‐derived, ‘water extract of pomegranate ash’ (WEPA), has been utilized for the first time as a renewable medium for Pd(OAc)2‐catalysed Suzuki–Miyaura cross‐coupling at room temperature. This method offers a simple and sustainable synthesis of biaryls from aryl halides and arylboronic acids under ligand‐ and external base‐free aerobic and ambient conditions. This method has been found effective for both activated and unactivated aryl halides in the production of biaryls with moderate to nearly quantitative yields. The protocol shows high chemoselectivity over identical/similar reactive sites in aryl halides (i.e. selectivity over identical halogens or different halogens of aryl halides). This method exhibits high regioselectivity, i.e. the selective reactivity of a halogen over other identical halogens at different positions on the aromatic nucleus. Therefore, we disclose here a clean, benign, substantial chemo‐ and regioselective and highly economic alternative method for the palladium‐assisted synthesis of biaryls using an agro waste‐derived medium.

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“…Various Pd‐catalyzed reactions viz. Suzuki‐Miyaura and Sonogashira coupling, popular name reactions (for example Dakin and Henry reaction) and other organic synthesis such as peptide synthesis, azidation of aromatics and synthesis of 3‐carboxycoumarins have been successfully performed in this green reaction medium. Although WEB can be used alone, in some cases it has been mixed with organic solvents like ethanol and iso ‐propanol to increase the miscibility of reagents and starting materials so that the reactions furnish higher yields of the products .…”

Section: Introductionmentioning

confidence: 99%

A Green Protocol for the Synthesis of α‐Diazo‐β‐hydroxyesters and One‐Pot Conversion to β‐Keto‐Esters and Imidazo[1,2‐a]pyridine‐3‐carboxylates

et al. 2019

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A new solvent cum reagent system comprising of water extract of banana ash and dimethylsulfoxide (WEB‐DMSO) has been engaged for the first time to promote the aldol type condensation reaction of aldehydes with ethyl diazoacetate. The condensation reaction has smoothly undergone producing a range of α‐diazo‐β‐hydroxy esters in good to excellent yields. The solvent system has been reused up to five times without loss of its catalytic activity. Further, two one‐pot sequential reactions have been developed in the same reaction medium. First, the methodology has been extended to synthesize β‐keto esters through Pd catalyzed 1,2‐hydrogen migration. Secondly, β‐keto esters have been converted to imidazo[1,2‐a]pyridine‐3‐carboxylates by using N‐bromosuccinimide and 2‐aminopyridines in a one‐pot fashion.

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A novel green protocol for ligand free Suzuki–Miyaura cross-coupling reactions in WEB at room temperature

Cited by 139 publications

References 38 publications

Water Phase, Room Temperature, Ligand‐Free Suzuki–Miyaura Cross‐Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage

Water Phase, Room Temperature, Ligand‐Free Suzuki–Miyaura Cross‐Coupling: A Green Gateway to Aryl Ketones by C–N Bond Cleavage

Palladium‐catalysed room‐temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio‐derived sustainable and renewable medium

A Green Protocol for the Synthesis of α‐Diazo‐β‐hydroxyesters and One‐Pot Conversion to β‐Keto‐Esters and Imidazo[1,2‐a]pyridine‐3‐carboxylates

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