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 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall

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.

Keywords: Brønsted acid; alcohols; alkenes; hydrogen-atom transfer; reduction

Domains: Chemical Sciences; Organic chemistry

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⟩