2021
DOI: 10.1021/acs.joc.1c02197
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Selective Acid-Catalyzed Hydroarylation of Nonactivated Alkenes with Aniline Assisted by Hexafluoroisopropanol

Abstract: The catalytic hydroarylation of nonactivated alkenes with aniline is a reaction of high interest, aiming at providing C-functionalized aniline derivatives that are important precursors for the fabrication of polyurethanes. However, this reaction remains a longstanding goal of catalysis, as it requires one to simultaneously address two important goals: (1) the very low reactivity of nonactivated alkenes and (2) control of the hydroarylation/hydroamination selectivity. As a result, the hydroarylation of aniline … Show more

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Cited by 7 publications
(4 citation statements)
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“…Different solvents including 1,4-dioxane, DMF, DMSO, DCE and MeCN were also investigated, and it was found that TFE was the more suitable than the others for this reaction (Table 1, entries [13][14][15][16][17]. Elevating the reaction temperature to 70 °C or 80 °C led to the formation of certain side products with decreased yields of olefin hydroamination products, whereas reducing the temperature also led to a low catalytic efficiency (Table 1, entries [18][19][20], therefore, the optimised temperature was 60 °C. Subsequently, a series of condition optimisations, including different Ni(II) sources, the ratios of 1a/2a, of Ni(II)/Sc(III), and the amount of the catalyst loading were investigated using TFE (see Tables S1-S4, ESI †).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Different solvents including 1,4-dioxane, DMF, DMSO, DCE and MeCN were also investigated, and it was found that TFE was the more suitable than the others for this reaction (Table 1, entries [13][14][15][16][17]. Elevating the reaction temperature to 70 °C or 80 °C led to the formation of certain side products with decreased yields of olefin hydroamination products, whereas reducing the temperature also led to a low catalytic efficiency (Table 1, entries [18][19][20], therefore, the optimised temperature was 60 °C. Subsequently, a series of condition optimisations, including different Ni(II) sources, the ratios of 1a/2a, of Ni(II)/Sc(III), and the amount of the catalyst loading were investigated using TFE (see Tables S1-S4, ESI †).…”
Section: Resultsmentioning
confidence: 99%
“…8,9 To date, catalytic addition of versatile olefins to anilines to construct the C-N bond for aniline derivative synthesis has been well documented, and a wide variety of noble metalbased catalysts, Lewis acid (LA) and Brønsted acid based catalysts have been explored. [10][11][12][13][14][15][16][17][18][19][20][21][22] For example, in 2000, Kawatsura and Hartwig reported a Pd(TFA) 2 catalysed hydroamination of styrene under acidic conditions (Scheme 1a). 23 In 2005, Bergman and co-workers developed a Brønsted acid catalysed synthesis with a PhNH 3 B(C 6 F 5 ) 4 •Et 2 O catalyst at an elevated temperature (135 °C) (Scheme 1b), 24 and in 2011 Li reported a Lewis acid, that is, Zn(OTf ) 2 , catalysed synthesis also at an elevated temperature (130 °C) (Scheme 1c).…”
Section: Introductionmentioning
confidence: 99%
“…Among various heavy main group element compounds, reactivity and catalysis of bismuth compounds are attracting recent interest because bismuth compounds exhibit organometallic reactivity and catalysis like transition metal complexes, and the toxicity of bismuth element is low, as discussed by recent review articles. Indeed, many catalytic reactions by bismuth compounds have been reported in the past decade. One of the interesting reactions is fluorination of arylboronic esters using bismuth redox catalysts reported by Cornella and co-workers. ,, This reaction is useful for the synthesis of fluorinated compounds. Also, the synthesis of arylsulfonyl fluorides by bismuth redox-neutral catalysts reported by the same group (Scheme ) is interesting for the following reasons: (1) organic sulfonyl fluoride is an important structural motif in chemical biology and pharmaceuticals and (2) various sulfur­(VI) compounds are useful for synthetic chemistry; for instance, exchange reaction with sulfur­(VI) fluoride is one of the good elementary steps of click chemistry. , …”
Section: Introductionmentioning
confidence: 99%
“…In contrast to protected amino groups of anilides, tertiary anilines and N -pyrimidyl anilines, the amino group of unprotected anilines would readily undergo classic and transition-metal-catalyzed nucleophilic substitution, leading to N -alkyl byproducts (Scheme C) . Furthermore, the less sterically hindered amino group normally leads to the production of both ortho - and para -isomers . Thus, unprotected anilines have always been challenging substrates.…”
Section: Introductionmentioning
confidence: 99%