Work

Regio and Stereoselective Multicomponent Palladium-Catalyzed Carbonylative Heck-Stille arylation of allylic alcohols derivatives

Year: 2026

Type: preprint

Abstract: A reliable and operationally simple protocol for the regioselective and enantioselective carbonylative Heck-Matsuda arylation of protected allylic alcohols followed by interception of the acyl–palladium intermediate with alcohols and organostannane in a Stille-type coupling was developed. This intermolecular carbonylative Heck method provides access to highly functionalized esters and methyl ketones with the formation of multiple carbon–carbon bonds and the construction of an all-carbon quaternary stereogenic center in a single step from readily available starting materials in good to excellent yields. The reaction displays a broad substrate scope, affording products that offer opportunities for further derivatization, including their conversion into enantioenriched functionalized furans.

Source: ChemRxiv

DOI: 10.26434/chemrxiv.15008033/v1

Authors: Sergei Aleksandrovich Gorbatov, Arnaldo Gomes de Oliveira Junior, Andrea Nastri de Luca Batista, João Marcos Batista Junior, Carlos Roque Duarte Correia

Institutions: Universidade Estadual de Campinas (UNICAMP), Universidade Federal Fluminense, Universidade Federal de São Paulo

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Fundação de Amparo à Pesquisa do Estado de São Paulo

Awards: CIBFar - Center for Innovation in Biodiversity and Drug Discovery, Self-sustaining enantioselective Heck-Matsuda reactions via diazonium salts generated in situ from anilines or nitroarenes in in-tandem or one-pot cascade strategies, Nuclear magnetic resonance spectroscopy: beyond molecular structure assignment

OpenAlex ID: W7204758511

Cites: 19

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Related to: 10