Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer

Dhika Aditya Gandamana (1) , Bin Wang (1) , Ciputra Tejo (1) , Benoit Bolte (2) , Fabien Gagosz (2, 3) , Shunsuke Chiba (1)

1 Nanyang Technological University [Singapour]
2 DCSO - Laboratoire de synthèse organique
3 University of Ottawa [Ottawa]

A new protocol for the deoxygenation of alcohols and the hydrogenation of alkenes under Brønsted acid catalysis has been developed. The method is based on the use of either a benzyl or isopropyl ether as a traceless hydrogen-atom donor, and involves an intramolecular hydride transfer as a key step, which is achieved in a regio- and stereoselective manner.

Mots clés: Brønsted acid; alcohols; alkenes; hydrogen-atom transfer; reduction

Domaines: Chimie organique

Dhika Aditya Gandamana, Bin Wang, Ciputra Tejo, Benoit Bolte, Fabien Gagosz, et al.. Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer. Angewandte Chemie International Edition, 2018, 57 (21), pp.6181-6185. ⟨10.1002/anie.201801953⟩. ⟨hal-02090660⟩