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• W2949492043 abstract "The preparation of allylic amines has been an area of considerable activity in recent years due primarily to their key function as intermediate in organic synthesis, 1 as well as their biological properties 2 and their presence in several natural products. 3 A number of synthetic methods for the preparation of allylic amines are now known. 4 Some representative examples include nucleophilic allylic substitutions 5 and allylic amination of alkenes. 6 In the course of our studies on the development of new synthetic methods using hypervalent iodine compounds, we have reported the synthetic method for the preparation of βketo phosphonates from silyl enol ethers using iodosobenzene, 7 allylation of aromatic compounds by the reaction of allylsilane with aromatic compounds using hypervalent iodine compound, 8 aziridination of vinylphosphonates using [ N-(ptoluenesulfonyl)imino]phenyliodinane (PhI=NTs), 9 and transformation of allylsilanes into allylic amines using PhI=NTs. 10 Herein we report the transformation of allylsilanes and allylstannanes into allylic amines using PhI=NTs as amination reagent in more details. Table 1 shows that the Lewis acid catalyzed amination of allylsilanes and allylstannanes with PhI=NTs provided moderate yields of allylic amines in both polar and nonpolar media. The reaction rate and the efficiency are enhanced when more polar solvent, such as acetonitrile, is employed. In solvents of lower polarity such as methylene chloride and benzene, the reactions are substantially slower and some cases provide lower yields of products. Amination of allylsilanes and allylstannanes with PhI=NTs did not proceed in the absence of Cu(OTf) 2. The yields when using catalytic Cu(OTf)2 (10 mmol) as the Lewis acid were higher than using 1 equiv. of BF 3·OEt2 (entry 1 and 3). In the presence of 10 mol % of Cu(OTf)2, a slight excess of the PhI=NTs (1.5 equiv.) reacted with allylsilanes and allylstannanes (the stoichiometrically limiting component except in entry 3) to form the N-tosylallyl amines. The use of 10 mol % of Cu(OTf)2 in acetonitrile at room temperature was found to be the optimal catalyst load-solvent combination for the amination of allylstannanes using PhI=NTs. As shown in Table 1, the yields are moderate, however, small amounts of the p-toluenesulfonamide were observed. This is thought to arise from the decomposition of PhI=NTs under the reaction conditions. On the basis of these results, we speculated that the reaction proceeds via allyliodine(III) intermediate (Scheme 2, a). The first step of the reaction is presumable the nucleophilic Table 1 . Preparation of allylic amines from allylsilanes and allylstannanes entry allyl reagents Lewis acid solvent time (h) yield (%) a products" @default.
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• W2949492043 date "2001-01-01" @default.
• W2949492043 modified "2023-09-24" @default.
• W2949492043 title "Lewis Acid-Catalyzed Allylic Amination of Allylsilanes and Allylstannanes with [N-(p-Toluenesulfonyl)imino]phenyliodinane" @default.
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