The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows selective and direct synthesis stilbenes from aryldiazonium salts mild temperature (20 °C). Mechanistic studies suggest radical pathway which DMF acts as initiator overall process.

Herein we report the formation and interesting reactivity of several azepino[4,5-b]indole heterocycles. Initially, a key intramolecular Heck reaction is used to efficiently create the azepino[4,5-b]indole seven membered ring containing an exocyclic double bond. Treatment of the olefin with ozone results in an unprecedented secondary reaction of the Criegee intermediate, through intramolecular o...

An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C cataly...

We describe herein a palladium-catalyzed Heck-type reaction of O-acetyl ketoximes and allylic alcohols to synthesise pyridines. This protocol allows the robust synthesis of pyridines and azafluorenones in good to excellent yields with tolerance of various functional groups under mild conditions. The reaction is supposed to go through an oxidative addition of oximes to palladium(0) complexes, ge...

Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3 )-Pd intermediate using diboron-water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectivities. When heavy water was used as a deuterium donor in combination with bis(catecholato)diboron (Cat2 B2 ), deuterium was incorporated into t...

[reaction: see text] The Heck reaction is a more efficient and reliable method than previous ones for introducing a C3 unit at the benzyl position for the synthesis of Beraprost. Especially, trialkylated long-chain amines such as (n-C(8)H(17))(3)N and (n-C(12)H(25))(3)N resulted in good yields. This development will be used for the industrial synthesis of Beraprost.

The “diverted Heck” reaction has been shown to be a potent method synthesize cyclopropanes from electron-rich olefins and iodomethyl trifluoroborate. Nevertheless, it is not mechanistically limited the three-membered rings. synthesis of five-membered rings using bifunctional substrates with halide moiety an organometallic group described. Furthermore, reactions respective boron tin-based are fu...