Nickel-catalyzed decarbonylative addition of anhydrides to alkynes.
نویسندگان
چکیده
An intermolecular nickel-catalyzed addition reaction has been developed where phthalic anhydrides react with alkynes to afford substituted isocoumarins. A mechanistic rationale is proposed, implying reductive elimination of Ni(0) promoted by ZnCl(2) cocatalyst as the key step of the catalytic cycle.
منابع مشابه
Ruthenium-catalyzed decarbonylative addition reaction of anhydrides with alkynes: a facile synthesis of isocoumarins and α-pyrones.
A novel ruthenium catalyzed straightforward and efficient synthesis of isocoumarin and α-pyrone derivatives has been accomplished by the decarbonylative addition reaction of anhydrides with alkynes under thermal conditions.
متن کاملNickel-catalyzed decarbonylative alkylidenation of phthalimides with trimethylsilyl-substituted alkynes.
We have developed a nickel-catalyzed transformation, in which phthalimides react with trimethylsilyl-substituted alkynes in the presence of Ni(0)/PMe3/MAD catalyst to provide isoindolinones. The reaction process displays an unusual mechanistic feature-decarbonylation and alkylidenation. The use of both trimethylsilyl-substiuted alkynes and MAD was found to be essential for the transformation wi...
متن کاملSelective synthesis of trienes and dienes via nickel-catalyzed intermolecular cotrimerization of acrylates and alkynes.
Tailoring nickel-catalyzed linear cotrimerization of acrylates and alkynes effectively proceeds to produce trienes and dienes highly selectively.
متن کاملMechanism, Reactivity, and Selectivity of Nickel-Catalyzed [4 + 4 + 2] Cycloadditions of Dienes and Alkynes
Density functional theory (DFT) calculations with B3LYP and M06 functionals elucidated the reactivities of alkynes and Z/E selectivity of cyclodecatriene products in the Ni-catalyzed [4 + 4 + 2] cycloadditions of dienes and alkynes. The Ni-mediated oxidative cyclization of butadienes determines the Z/E selectivity. Only the oxidative cyclization of one s-cis to one s-trans butadiene is facile a...
متن کاملNickel-catalyzed hydrocarboxylation of alkynes with formic acid†
Acrylic acid is an important commodity chemical and is widely used as a base material for the industrial production of paints, plastics, superabsorbent polymers, rubber, and so on. Currently acrylic acid is produced by partial oxidation of propene, which is refined from petroleum. Catalytic hydrocarboxylation of acetylene with CO is another way to synthesize acrylic acid with high atom-economy....
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Journal of the American Chemical Society
دوره 130 51 شماره
صفحات -
تاریخ انتشار 2008