Synthesis of α-Benzotriazole Selenides and Tellurides Promoted by Samarium Diiodide

Properties and Synthetic Utility ofN-Substituted Benzotriazoles

“…Reaction of 1-(chloromethyl)benzotriazole with diorganyl diselenides or diorganyl ditellurides in the presence of SmI 2 results in the formation of α-benzotriazol-1-yl-substituted unsymmetrical selenides 435 and tellurides 436 , respectively (Scheme , Table ), which can be subjected to further transformations to various α-functionalized selenides and tellurides 142 Benzotriazolylmethylation of Diselenides and Ditellurides 46 Preparation of Unsymmetrical Selenides 435 and Tellurides 436 compoundRyield, %compoundRyield, % 435 Et 80 435 Ph 75 Me 2 CHCH 2 78 4-ClC 6 H 4 72 n -Bu 82 c-C 6 H 11 76 n -C 5 H 11 81 436 Ph 80 n -C 6 H 13 80 4-MeC 6 H 4 83 …”

“…Reaction of 1-(chloromethyl)benzotriazole with diorganyl diselenides or diorganyl ditellurides in the presence of SmI 2 results in the formation of R-benzotriazol-1-yl-substituted unsymmetrical selenides 435 and tellurides 436, respectively (Scheme 142, Table 46), which can be subjected to further transformations to various R-functionalized selenides and tellurides. 254 N-(Benzotriazol-1-ylmethyl)heterocycles are readily prepared in good yields by heating the corresponding N-H heterocycles with 1-(chloromethyl)benzotriazole under basic conditions (Scheme 143).…”