Multifaceted catalysis approach to nitrile activation: direct synthesis of halogenated allyl amides from allylic alcohols.
نویسندگان
چکیده
Allyl amides were synthesised from the reaction of allyl alcohols and halogenated nitriles using a platinum multifaceted catalysis approach in which both the nucleophilic addition and subsequent [3,3]-sigmatropic rearrangement steps of the process were catalysed by the same complex. Additionally, (1)H/(13)C{(1)H} NMR and GC studies provided the first insights into the mechanism of this transformation.
منابع مشابه
Conversion of Alcohols into Amides Using Alumina-Methanesulfonic Acid (AMA) in Nitrile Solvents
The reaction of tertiary, secondary and benzylic alcohols with different nitriles in the presence of alumina-methanesulfonic acid (AMA) as a new reagent affords the corresponding amides in good yields (Table 1, 2). Conversion of 2,6-bis(hydroxymethyl)-4-halo anisoles into corresponding diamides in the range of 68-76% yields (Table 3) are also included in this paper.
متن کاملTandem synthesis of 3-allyl-chromones from alkynones and allylic alcohols under metal-free conditions.
A novel and efficient approach to 3-allyl-chromones from alkynones and allylic alcohols via a tandem Michael addition-Claisen rearrangement-O-arylation reaction has been developed. Diversely structural 3-allyl-chromones were afforded in up to 93% yield for 24 examples. This synthetic strategy is regiospecific, highly efficient, environment friendly and metal-free.
متن کاملA Mechanistic Study of Direct Activation of Allylic Alcohols in Palladium Catalyzed Amination Reactions
We here report a computational approach on the mechanism of allylicamination reactions using allyl-alcohols and amines as the substrates and phosphoramidite palladium catalyst 1a, which operates in the presence of catalytic amount of 1,3-diethylurea as a co-catalyst. DFT calculations showed a cooperative hydrogen-bonding array between the urea moiety and the hydroxyl group of the allyl alcohol,...
متن کاملRuthenium-catalyzed regio- and enantioselective allylic substitution with water: direct synthesis of chiral allylic alcohols.
Enantioselective allylic substitution catalyzed by transitionmetal complexes is an important process in organic synthesis. For many years, mainly palladium complexes that contain chiral ligands have been employed as efficient catalysts in these reactions. Recent studies have demonstrated that chiral catalysts based on other transition metals show different regioselectivity in the synthesis of b...
متن کاملRegio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols.
A hydroxyl group-directed, highly regio- and stereoselective transposition of allylic alcohols based on rhenium catalysis has been developed. The method is suitable for a direct isomerization of acetals into the thermodynamically preferred isomer as long as one of the hydroxyl groups is allylic. This method will expand the scope of rhenium-catalyzed alcohol transpositions for complex molecule s...
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:
- Organic & biomolecular chemistry
دوره 11 43 شماره
صفحات -
تاریخ انتشار 2013