Asymmetric alkyl-alkyl coupling between electron-deficient and unactivated alkenes to access α-chiral phosphines by Ni catalysis
Year: 2025
Type: article
Abstract: α-Chiral phosphorus compounds have broad applications as organic catalysts or ligands in organic chemistry and related areas. Herein, we disclose a Ni-catalyzed enantioselective cross-hydrodimerization of alkenyl phosphine sulfides with unactivated alkenes to access α-chiral phosphine sulfides, representing the first example of asymmetric hydrodimerization of electron-deficient alkenes with electron-rich alkenes. Key to success is the precise recognition between electron-deficient alkenes and electron-rich alkenes and streamlined alkyl-alkyl bond forming with the control of chemo-, regio-, and enantioselectivity. This strategy requires alkenes as sole precursors for asymmetric alkyl-alkyl cross-coupling, circumventing the use of stoichiometric amounts of alkyl electrophiles or alkyl nucleophiles as coupling partners. The mild conditions tolerate a wide range of functional groups, providing direct access to α-chiral phosphines through a carbon-carbon bond-forming process without prefunctionalized coupling precursors.
Source: Science Advances
Authors: Jian-Yu Zou, Fang-Li Xing, Quan-Xing Zi, Hai-Wu Du, Meiwan Chen, Wei Shu
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $4,500
OpenAlex ID: W4411259039