Other arene substrates were also tested using 5 cycles of Me3SiBraddition (Fig. 5c), with a yield of benzene to PhN(SiMe3)2 of (68 ± 4)%per iron. Toluene gave a mixture of (m-tolyl)N(SiMe3)2 and (p-tolyl)N(SiMe3)2 in a 3:1 ratio with a total yield of (61 ± 7)% per iron. The overallyield is similar to that for benzene, and the ratio of isomers is comparable to that observed in the crystal of LFe(H)(Tol)Na(15c5) (Supplementary Fig. 54). When o-xylene was used, a (12 ± 2)% yield of N,N-bis(trimethylsilyl-3,4-xylidine) was observed. These silylated aniline products could be hydrolysed to the deprotected anilines with weak aqueousacid when desired. Arenes with easily reducible functionalities—such asaryl halides, aryl ethers and polycyclic aromatics—did not give aminatedproducts. Formation of the silylated aniline and N(SiMe3)3 also occurredwith other Me3SiX reagents (X = Cl, I, OTf), although the reaction gavethe highest yields with Me3SiBr
Other arene substrates were also tested using 5 cycles of Me3SiBr<br>addition (Fig. 5c), with a yield of benzene to PhN(SiMe3)2 of (68 ± 4)%<br>per iron. Toluene gave a mixture of (m-tolyl)N(SiMe3)2 and (p-tolyl)<br>N(SiMe3)2 in a 3:1 ratio with a total yield of (61 ± 7)% per iron. The overall<br>yield is similar to that for benzene, and the ratio of isomers is comparable to that observed in the crystal of LFe(H)(Tol)Na(15c5) (Supplementary Fig. 54). When o-xylene was used, a (12 ± 2)% yield of N,N-bis<br>(trimethylsilyl-3,4-xylidine) was observed. These silylated aniline products could be hydrolysed to the deprotected anilines with weak aqueous<br>acid when desired. Arenes with easily reducible functionalities—such as<br>aryl halides, aryl ethers and polycyclic aromatics—did not give aminated<br>products. Formation of the silylated aniline and N(SiMe3)3 also occurred<br>with other Me3SiX reagents (X = Cl, I, OTf), although the reaction gave<br>the highest yields with Me3SiBr
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