2005
DOI: 10.1080/17415990500088997
|View full text |Cite
|
Sign up to set email alerts
|

An efficient one-pot Michael addition of dithiocarbamate anion to α,β-unsaturated olefins mediated by lithium perchlorate

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1

Citation Types

0
6
0

Year Published

2009
2009
2021
2021

Publication Types

Select...
8

Relationship

0
8

Authors

Journals

citations
Cited by 16 publications
(6 citation statements)
references
References 25 publications
0
6
0
Order By: Relevance
“…Because of our interest in studying the Michael reaction under solventfree and environmentally benign methods, [28][29][30][31][32] herein we report a mild, easy, and catalytic process for Michael addition of aromatic amines at 60 C and aliphatic amines at room temperature in excellent to quantitative yields using silica-supported aluminum chloride as catalyst. At first, we examined the reaction of aniline with methyl acrylate and 0.2 g of silica-supported aluminum chloride at room temperature under solventfree conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Because of our interest in studying the Michael reaction under solventfree and environmentally benign methods, [28][29][30][31][32] herein we report a mild, easy, and catalytic process for Michael addition of aromatic amines at 60 C and aliphatic amines at room temperature in excellent to quantitative yields using silica-supported aluminum chloride as catalyst. At first, we examined the reaction of aniline with methyl acrylate and 0.2 g of silica-supported aluminum chloride at room temperature under solventfree conditions.…”
Section: Resultsmentioning
confidence: 99%
“…Traditionally, a portion of dithiocarbamates were prepared through the reactions of amines, thiophosgene, isothiocyanate [12] or the combination of amines, carbon monoxide and sulfur [13] . Recently, the three‐component reactions of amines, carbon disulfide, and electrophilic alkenes have been reported by Guo, [14] Saidi, [15] Azizi, [16] Jerome, [17] Li, [18] Veignie [19] and Singh, [20] respectively (Scheme 1, a). However, the well‐known methodologies suffer from some drawbacks, such as foul‐smelling substrates, costly metal catalysts and harsh reaction conditions.…”
Section: Figurementioning
confidence: 99%
“…A similar yield of product 3 a was obtained when the reaction performed in the absence of copper catalyst (entry 2), but no product was observed in this reaction when it carried out under base-free conditions (entry 3). Based on this result, the effect of other bases were evaluated, and the results indicated that CsOAc was obviously superior to the others, providing 3 a in [12][13][14][15][16][17][18][19][20] revealed that all of these solvents are not as suitable as 1,4-dioxane. Gratifyingly, decreasing the reaction temperature to 90 °C resulted in a significant improving of the reaction yield (95%) of 3 a (entry 21).…”
mentioning
confidence: 99%
“…114 As well as thiols, dithiocarbamate anion can be added to R,β-unsaturated olefins by solid lithium perchlorate catalysis. 115 In fact, primary or secondary amines can react with carbon disulfide and olefins carrying electron-withdrawing groups in one pot and in good to high yields (85-95%) except for highly hindered carbonyl compounds (Scheme 40). Zinc perchlorate is as effective as LiClO 4 catalyst except for crowded unsaturated compounds and, moreover, the addition of aryl thiols occurs more rapidly than that of alkyl ones, showing also a dependence of the reaction on electronic factors.…”
Section: Conjugate Addition Of Alcoholates or Thiols (Thia-michael)mentioning
confidence: 99%