RESUMO
The only known method for the dearomative trifluoromethoxylation of indoles is preliminary, with only one substrate successfully undergoing the reaction. In this study, we not only developed a broadly applicable method for indole dearomative trifluoromethoxylation but also achieved divergent trifluoromethoxylation by fine-tuning the reaction conditions. Under optimized conditions, with a silver salt and an easily handled OCF3 reagent, various indoles smoothly underwent dearomatization to afford a diverse array of ditrifluoromethoxylated indolines in 50-84% isolated yields with up to 37:1 diastereoselectivity, and fluorinated trifluoromethoxylated indolines were obtained with exclusive trans selectivity. In addition, the reaction conditions were compatible with other heteroaromatic rings as well as styrene moieties.
RESUMO
An efficient direct nucleophilic addition reaction of C(sp2)-H bonds to aldehydes catalyzed by a dimeric manganese has been developed. This reaction has a broad range of substrates, and high yields were also obtained with inert aliphatic aldehydes as substrates. A dimeric Mn2(CO)8Br2 was proven to be a more efficient catalyst precursor than the monomeric Mn(CO)5Br.