Palladium-catalysed direct arylations of heteroaromatics using more eco-compatible solvents pentan-1-ol or 3-methylbutan-1-ol

Bensaid, Souhila; Laidaoui, Nouria; Abed, Douniazad El; Kacimi, S.; Doucet, Henri

doi:10.1016/j.tetlet.2011.01.084

Cited by 22 publications

(9 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In recent years, a few solvents which can be considered as “green” according to P. Anastas principles, have been employed for Pd‐catalysed direct arylations of heteroaromatics . For example, water was employed by Greaney and Djakovitch for the arylation of some 5‐membered ring heterocycles; whereas, Ackermann employed a polyethylene glycol solvent for the direct arylation of triazoles .…”

Section: Introductionmentioning

confidence: 99%

“…For example, water was employed by Greaney and Djakovitch for the arylation of some 5‐membered ring heterocycles; whereas, Ackermann employed a polyethylene glycol solvent for the direct arylation of triazoles . Carbonates, ethers or alcohols have been used as the solvents for the arylation of heteroarenes . All these reactions were performed using homogeneous Pd‐catalysts.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

2018

Self Cite

View full text Add to dashboard Cite

Metal residues are certainly one of the major sources of contamination of products in metalcatalyzed direct arylation reactions. We found that the use of only 1 mol% of the heterogeneous catalyst Pd/C promotes very efficiently the direct arylations of most heteroaromatics. In the presence of this catalyst and potassium acetate as the base, the direct arylation of thiophenes, furans, pyrroles, thiazoles, imidazoles or isoxazoles, using aryl bromides as coupling partners, proceeds highly regioselectively and in moderate to very high yields. With several heteroarenes both electron-deficient and electron-rich aryl bromides were tolerated; moreover, with the most reactive heteroarenes, the Pd/C catalyst tolerated green solvents such as diethyl carbonate, 3-methylbutan-1-ol and pentan-1-ol, affording a synthetic scheme with low environmental impact.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…In 2011, our group reported that thiazoles and imidazoles can be arylated at C5‐position with a range of aryl bromides using 3‐methylbutan‐1‐ol or pentan‐1‐ol as the solvents with 2 mol% of PdCl(C 3 H 5 )(dppb) catalyst (Scheme ) . We also investigated the C3‐arylation of imidazo[1,2‐ b ]pyridazines in pentan‐1‐ol (Scheme ) .…”

Section: Reactions In Green Solventsmentioning

confidence: 99%

“…[29] In 2016, GVL has been evaluated by Ackermann, Vaccaro et al for the direct arylation of 1,2,3-triazoles (Scheme 17). [30] They employed Pd/C (5 mol%) as catalyst and aryl bromides as aryl source, and obtained the C5arylated 1,2,3-triazoles in good yields.…”

Section: Reactions In G-valerolactonementioning

confidence: 99%

“…We have seen in the section 2.5, that Pd/C (5 mol%) catalyst was successfully employed by Ackermann, Vaccaro et al for the direct C5-arylation of 1,2,3-triazoles using g-valerolactone as green solvent (Scheme 17). [30] In 2014, Glorius group extended the scope of Pd/C catalyst using green solvents to the C4-arylation of thiophenes employing aryliodonium salts as aryl source instead of aryl chlorides, but without copper salt as additive (Scheme 27). [43b] These reactions were performed in ethanol at only 60 8C.…”

Section: Reactions With Pd/c Catalyst In Green Solventsmentioning

confidence: 99%

See 1 more Smart Citation

Environmentally Benign Arylations of 5‐Membered Ring Heteroarenes by Pd‐Catalyzed C−H Bonds Activations

Mao

Shi

et al. 2018

ChemCatChem

Self Cite

View full text Add to dashboard Cite

The palladium‐catalyzed functionalization of 5‐membered ring heteroaromatics, through a C−H bonds activation, for access to arylated heteroaromatics represent a very attractive alternative to more classical cross‐coupling reactions, as it saves steps and reduces the amount of wastes. Despite these advantages, these transformations initially suffered from major limitations in terms of sustainable chemistry concerning the reaction media, the nature of the catalyst, the catalyst loading, the aryl source or the regioselectivity control. Tremendous improvements allowing more sustainable reaction conditions using greener solvents, new aryl sources or employing easily removable catalysts and lower catalyst loadings have been described during the last decades. This review summarizes some of the most important contributions made in these directions.

show abstract

Functionalization of Five‐membered Heterocycles with Two Heteroatoms

Joo¹

2023

Transition‐Metal‐Catalyzed C‐H Functionalization of Heterocycles

View full text Add to dashboard Cite

Palladium-catalysed direct arylations of heteroaromatics using more eco-compatible solvents pentan-1-ol or 3-methylbutan-1-ol

Cited by 22 publications

References 62 publications

Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

Environmentally Benign Arylations of 5‐Membered Ring Heteroarenes by Pd‐Catalyzed C−H Bonds Activations

Functionalization of Five‐membered Heterocycles with Two Heteroatoms

Contact Info

Product

Resources

About