Late-Stage Derivatization of Buflavine by Nickel-Catalyzed Direct Substitution of a Methoxy Group via C–O Bond Activation

Abstract

The nickel-catalyzed cross-coupling of methoxyarenes is applied to buflavine, which allows for the selective mono-substitution of one of the two methoxy groups in the molecule, leading to the formation of 2- and 3-substituted isomers. Trimethylsilylmethyl (TMSCH2), phenyl and alkynyl groups can be introduced to buflavine using this method. The resulting TMSCH2 analog of buflavine can also be converted into several other derivatives.

Speciation and kinetics of fluoride transfer from tetra-n-butylammonium difluorotriphenylsilicate (‘TBAT’)

“…Tetra- n -butylammonium difluorotriphenylsilicate (TBAT, Fig. 1) was introduced by DeShong 1 in 1995 as a convenient alternative to tetra- n -butylammonium fluoride (TBAF), and is widely employed, inter alia , for C–F generation, 1 a ,2 deprotection, 3 benzyne generation, 4 and anion generation by Si–X cleavage (X = C, 5 N, 6 O, 7 S; 7 d ). 8,9…”