Blue Light Enhanced Heck Arylation at Room Temperature Applied to Allenes

An unprecedented visible light enhanced room temperature Heck reaction between aryl halides and allenyl tosyl amines is here reported. The simple catalytic system (Pd(OAc)2/PPh3) is exploited to afford arylated vinyl...

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium salts via regioselective Heck arylation at room temperature

Synthesis of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described at room temperature. The reaction is catalyzed by palladium acetate in the absence of ligands and base.

Matsuda-Heck arylation of itaconates: a versatile approach to heterocycles from a renewable resource

Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in...

The influence of additives on orthogonal reaction pathways in the Mizoroki-Heck arylation of vinyl ethers

The Mizoroki-Heck arylation of electron-rich alkenes such as butyl vinyl ether often results in regioisomeric mixtures of products under typical reaction conditions. To discover new catalytic systems for achieving α-selective...

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.