Modification of Natural Eudesmane Scaffolds via Mizoroki-Heck Reactions.
نویسندگان
چکیده
The Mizoroki-Heck reaction was applied to substrates derived from isocostic and ilicic acids, important sesquiterpene components of Dittrichia viscosa L. Greuter that were extracted directly from plant material collected in Morocco. After optimization of the metallo-catalysis conditions, various aryl-groups were successfully introduced on the exocyclic double bond with an exclusive E-configuration and without racemization.
منابع مشابه
Synthesis, Characterization and Catalytic Study of a Novel Binuclear Paddle-wheel Palladium(II) Complex in the Mizoroki-Heck Reaction
A new binuclear paddle-wheel palladium(II) complex of [Pd2(μ-mtzt)4]dmgH2 (1) has been prepared by the treatment of PdCl2 in acetonitrile with mixture of 1-methyl-1H-1,2,3,4-tetrazole-5-thiol (Hmtzt) and dimethylglyoxime (dmgH2) in methanol. Resulted complex was characterized by elemental analysis (CHNS), IR, UV–Vis absorption, 1H NMR spectroscopy and its structure was determined with single-cr...
متن کاملMechanisms of the Mizoroki–Heck Reaction
The palladium-catalysed Mizoroki–Heck reaction is the most efficient route for the vinylation of aryl/vinyl halides or triflates. This reaction, in which a C C bond is formed, proceeds in the presence of a base (Scheme 1.1) [1, 2]. Nonconjugated alkenes are formed in reactions involving cyclic alkenes (Scheme 1.2) [1e, 2a,c,e,g] or in intramolecular reactions (Scheme 1.3) [2b,d–g] with creation...
متن کاملReactions of nitroxides 15. Cinnamates bearing a nitroxyl moiety synthesized using a Mizoroki–Heck cross-coupling reaction
Cinnamic acid derivatives bearing a nitroxyl moiety (2,2,6,6-tetramethyl-1-oxyl-4-piperidyl 3-E-aryl acrylates) were synthesized in 30-100% yield using a Mizoroki-Heck cross-coupling reaction between 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl and iodobenzene derivatives in the presence of palladium(II) acetate coordinated with a tri(o-tolyl)phosphine ligand immobilized in a polyurea mat...
متن کاملSynthesis, characterization and microwave-promoted catalytic activity of novel N-phenylbenzimidazolium salts in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under mild conditions.
A number of novel benzimidazolium salts having aryl substituents such as N-phenyl, 4-chlorophenyl and various alkyl substituents were synthesized. Their microwave-assisted catalytic activities were evaluated in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions using a catalytic system consisting of Pd(OAc)(2)/K(2)CO(3) in DMF/H(2)O under mild reaction conditions with consistent high y...
متن کاملBreaking the regioselectivity rule for acrylate insertion in the Mizoroki-Heck reaction.
In modern methods for the preparation of small molecules and polymers, the insertion of substrate carbon-carbon double bonds into metal-carbon bonds is a fundamental step of paramount importance. This issue is illustrated by Mizoroki-Heck coupling as the most prominent example in organic synthesis and also by catalytic insertion polymerization. For unsymmetric substrates H(2)C = CHX the regiose...
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:
- Molecules
دوره 22 4 شماره
صفحات -
تاریخ انتشار 2017