Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with N-Heterocyclic Nucleophiles.
نویسندگان
چکیده
The development of a decarboxylative palladium-catalyzed coupling of 1,3-dicarbonyl compounds with indole, pyrrole, imidazole, and pyrazole nucleophiles via an allylic linker under neutral conditions is disclosed. This process enables the installation of an all-carbon quaternary center and new C-C and C-N bonds in a single operation. Despite the weakly acidic nature of N-heterocycles, the reactions proceed with good efficiency and complete regio- and chemoselectivity.
منابع مشابه
Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water
Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.
متن کاملN-heterocyclic carbene-catalyzed 1,3-dipolar cycloaddition reactions: a facile synthesis of 3,5-di- and 3,4,5-trisubstituted isoxazoles.
A first example of organo-N-heterocyclic carbene (NHC) catalyzed click-type fast 1,3-dipolar cycloaddition of nitrile oxides with alkynes was developed for the regioselective synthesis of 3,5-di- and 3,4,5-trisubstituted isoxazoles. Triethylamine (Et(3)N) was employed as an effective base to generate both nitrile oxide and the organo-NHC catalyst in situ. This catalytic approach was used to att...
متن کاملSOLVENT-FREE SYNTHESIS OF PYRROL DERIVATIVES USING MULTICOMPONENT REACTIONS OF 1,3-DICARBONYLS, ACTIVATED CARBONYL COMPOUNDS, AND PRIMARY ALKYLAMINES
one-pot synthesis of pyrrole derivatives via reaction between activated carbonyl compounds, primary amines and 1,3-dicarbonyls under solvent-free conditions is described.
متن کاملSOLVENT-FREE SYNTHESIS OF PYRROL DERIVATIVES USING MULTICOMPONENT REACTIONS OF 1,3-DICARBONYLS, ACTIVATED CARBONYL COMPOUNDS, AND PRIMARY ALKYLAMINES
A one-pot synthesis of pyrrole derivatives via reaction between activated carbonyl compounds, primary amines and 1,3-dicarbonyls under solvent-free conditions is described.
متن کاملAsymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.
A one-pot, asymmetric multicatalytic formal [3+2] reaction between 1,3-dicarbonyls and alpha,beta-unsaturated aldehydes is described. The multicatalytic process involves a secondary amine catalyzed Michael addition followed by a N-heterocyclic carbene catalyzed intramolecular crossed benzoin reaction to afford densely functionalized cyclopentanones with high enantioselectivities. The reaction p...
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:
- The Journal of organic chemistry
دوره 81 12 شماره
صفحات -
تاریخ انتشار 2016