Alkynylsilanes and allyltrimethylsilane undergo smooth coupling with acid chlorides in the presence of 5 mol% of indium tribromide under mild conditions to afford the corresponding a,bacetylenic ketones and b,g-unsaturated ketones in excellent yields in a short reaction time with high selectivity.
Pyrrole reacts smoothly with terminal epoxides in the presence of a catalytic amount of InBr 3 under very mild conditions to afford the corresponding C-alkylated pyrroles in high yields. Similarly, activated aziridines also opened by pyrrole under the influence of indium tribromide to afford 2-and 3-alkyl pyrrole derivatives in high yields with high regioselectivity.
Aryl- N-tosylaziridines and epoxides smoothly undergo ring-opening with pyrrole and indoles in the presence of 5M lithium perchlorate in diethyl ether (LPDE) at ambient temperature to afford the corresponding 2- and 3-alkylated pyrroles and 3-alkylated indoles in high yields with high selectivity. LiOTf is also found to be an effective catalyst for this transformation.
Aziridines react smoothly with sodium azide and sodium cyanide in the presence of catalytic amount of lithium perchlorate under essentially mild and neutral reaction conditions to afford the corresponding b-azido and b-cyanoamines in high yields with high regioselectivity.
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