2008
DOI: 10.1016/j.tet.2008.09.099
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Sn(OTf)2 catalysed regioselective styrene oxide ring opening with aromatic amines

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Cited by 30 publications
(11 citation statements)
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“…In the presence of protic or Lewis acids, amines, even the less reactive aromatic ones, can open the three‐membered oxirane ring. Various metal salts have been used as catalysts in synthetic procedures, including Sn II bistrifluoromethanesulfonate, which successfully mediates the reaction of epoxides with both aliphatic and aromatic amines 64. It can, therefore, be assumed that the ligands used in ARGET ATRP can participate in similar reactions in the presence of Sn II compounds or the products of their oxidation by Cu II , Sn IV compounds, which are characterized by even higher Lewis acidity.…”
Section: Resultsmentioning
confidence: 99%
“…In the presence of protic or Lewis acids, amines, even the less reactive aromatic ones, can open the three‐membered oxirane ring. Various metal salts have been used as catalysts in synthetic procedures, including Sn II bistrifluoromethanesulfonate, which successfully mediates the reaction of epoxides with both aliphatic and aromatic amines 64. It can, therefore, be assumed that the ligands used in ARGET ATRP can participate in similar reactions in the presence of Sn II compounds or the products of their oxidation by Cu II , Sn IV compounds, which are characterized by even higher Lewis acidity.…”
Section: Resultsmentioning
confidence: 99%
“…[9,33,34] For example, in the case of para-nitroaniline, for both catalysts 2 and 3, the yield dropped to less than 10 % (Entry 6) even when the reaction was carried out for 24 h as compared to 4 h in other cases. To determine the regioselectivity, styrene oxide was used as a representative unsymmetrical epoxide [33,34] and was treated with aniline or para-substituted anilines in the presence of catalyst 2 or 3 (5 mol-%; Table 4). Interestingly, a perfect regioselectivity was observed that resulted in only a single product in all cases with both catalysts 2 and 3.…”
Section: Solvent-free Catalytic Applications Of Network 2 Andmentioning
confidence: 99%
“…The synthetic route for such compounds commonly proceeds via ring-opening of oxiranes (epoxides) using traditional Lewis acids such as Cu(BF 4 ) 2 [2,21], Sn(OTf) 2 [11], BF 3 [22], Sc(OTf) 3 [24], and traditional solid acids such as amberlyst-15 [10]. Modified Lewis acid complexes based on salen [5,12] and porphyrin [23] ligands have also been reported.…”
Section: Introductionmentioning
confidence: 99%