Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.
نویسندگان
چکیده
Various highly substituted 2,3'-diindolylmethane heterocycles were prepared from propargylic alcohols and indole nucleophiles via a transition metal-catalyzed tandem indole annulation/arylation reaction for the first time. Among the metal catalysts we examined, the most economical copper(I) catalyst provided the highest efficiency. The indole nucleophiles could also be replaced by other electron-rich arenes or alcohols.
منابع مشابه
Silver(I)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols.
A regioselective efficient synthetic approach to N-imino-γ-carbolinium ylides via AgOTf-catalyzed iminoannulation has been developed. This transformation proceeds via a silver(i) triflate-catalyzed consecutive Friedel-Crafts reaction/N-C bond formation sequence between the readily available indole derivatives and propargylic alcohols.
متن کاملUrea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
متن کاملUrea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
متن کاملTransition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
The base-catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1-disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid-base adduct, [Hbase](+) [MeO-B2 pin2 ](-) favored the formation of 1,2,3-triborylated species from the tertiary allylic alcohols and 1-propargylic cyclohexanol at 90 °C.
متن کاملSilver-catalyzed cascade reaction of tosylmethyl isocyanide (TosMIC) with propargylic alcohols to (E)-vinyl sulfones: dual roles of TosMIC.
An unprecedented silver-catalyzed cascade reaction of tosylmethyl isocyanide (TosMIC) with propargylic alcohols for the efficient synthesis of (E)-vinyl sulfones has been developed where TosMIC plays a dual role as both the reactant in the allenylation of propargylic alcohols and the sulfonyl source.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 82 شماره
صفحات -
تاریخ انتشار 2014