Electrooxidative Pd-Catalyzed Remote Hydrofunctionalization of Alkenes with Nucleophiles

ACS Catalysis, Год журнала: 2024, Номер 14(21), С. 15858 - 15868

Опубликована: Окт. 11, 2024

The catalytic hydrofunctionalization of alkenes with nucleophiles via the generation carbocationic intermediates has been extensively studied as an efficient strategy for regioselective installation functional groups on alkene feedstocks. However, since established methods are confined to functionalization position where is originally located, it highly desirable develop a broadly applicable platform that offers alternative regioselectivity otherwise challenging achieve existing protocols. Herein, we report remote method enabled by electrooxidative palladium hydride catalysis. key success formation carbocation intermediate through mechanistic pathway, which involves chain-walking process followed anodic oxidation organopalladium species. This allows terminal and internal broad range oxygen, carbon, nitrogen, fluoride nucleophiles, including complex drug-like molecules.

Язык: Английский

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Electricity‐Driven Strain‐Release Cascade Cyclization of Bicyclo[1.1.0]butane (BCB): Stereoselective Synthesis of Functionalized Spirocyclobutyl Oxindoles

ChemSusChem, Год журнала: 2024, Номер unknown

Опубликована: Окт. 23, 2024

Abstract Spirocyclobutyl oxindoles, characterized by their unique three‐dimensional structures, are valuable building blocks for many pharmacophores and drug units. However, stereoselective synthetic strategies these scaffolds remain underdeveloped, with most existing methods relying on transition metal catalysts stoichiometric redox reagents. In this work, we introduce an electrochemical strain‐release driven cascade spirocyclization of bicyclo[1.1.0]butane (BCB) derivatives the synthesis functionalized spirocyclobutyl oxindoles. Tetrabutylammonium bromide serves a dual purpose as both supporting electrolyte brominating agent. The method offers broad substrate scope, high atom economy, excellent diastereoselectivity. stereoselectivity product is controlled minimizing dipolar repulsion between amide C=O C−Br bonds. We also explored methodology′s versatility applying it to various functionalizations demonstrated its scalability practical use. efficient derivatization products allowed rapid creation diverse library

Язык: Английский

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An effective alliance for successful coupling: electrochemical alcohol oxidation mediated conversion of indoles to bis(indolyl)methanes

Journal of Applied Electrochemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 21, 2024

Язык: Английский

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