Nickel-catalyzed [4+2] cycloaddition for highly substituted arenes.
نویسندگان
چکیده
Nickel(0) catalyzed [4+2] cycloaddition of electron-deficient dienes to alkynes and subsequent aromatization gave highly substituted arenes. This formal inverse electron-demand Diels-Alder cycloaddition is attributed to the formation of a seven-membered nickelacycle from a diene and an alkyne.
منابع مشابه
Facile synthesis of 5-substituted-1H-tetrazoles catalyzed by reusable nickel zirconium phosphate nanocatalyst
5-Substituted-1H-tetrazoles were synthesized by the [3 + 2] cycloaddition of sodium azide with various nitriles in the presence of nickel zirconium phosphate (NiZrP) as an effective heterogeneous catalyst in dimethylsulfoxide at 120 °C. This method has the advantages of good to high yields, simple methodology and easy work-up. The catalyst can be recovered by centrifuging and reused with good y...
متن کاملFacile synthesis of 5-substituted-1H-tetrazoles catalyzed by reusable nickel zirconium phosphate nanocatalyst
5-Substituted-1H-tetrazoles were synthesized by the [3 + 2] cycloaddition of sodium azide with various nitriles in the presence of nickel zirconium phosphate (NiZrP) as an effective heterogeneous catalyst in dimethylsulfoxide at 120 °C. This method has the advantages of good to high yields, simple methodology and easy work-up. The catalyst can be recovered by centrifuging and reused with good y...
متن کاملNickel-catalyzed borylation of arenes and indoles via C-H bond cleavage.
The first nickel-catalyzed method for the borylation of carbon-hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.
متن کاملNickel-Catalyzed Intramolecular [3 + 2 + 2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5-Tricyclic Systems
A highly diastereo- and chemoselective intramolecular nickel-catalyzed cycloaddition of alkene- and alkyne-tethered alkynylidenecyclopropanes is reported. The method constitutes the first fully intramolecular [3 + 2 + 2] alkylidenecyclopropropane cycloaddition occurring via a proximal cleavage of the cyclopropane and makes it possible to build relevant 6,7,5-tricyclic frameworks in a single-pot...
متن کاملOrganocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans.
Highly substituted 4H-pyrans can be smoothly synthesized from readily available 2-(1-alkynyl)-2-alkene-1-ones by DBU- or n-Bu(3)P catalyzed hetero-[4+2] cycloaddition reactions, in which 2-(1-alkynyl)-2-alkene-1-ones act as both heterodiene and heterodinenophile.
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 48 32 شماره
صفحات -
تاریخ انتشار 2012