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

Dhika Aditya Gandamana; Bin Wang; Ciputra Tejo; Benoit Bolte; Fabien Gagosz; Shunsuke Chiba

doi:10.1002/anie.201801953

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

Angew Chem Int Ed Engl. 2018 May 22;57(21):6181-6185. doi: 10.1002/anie.201801953. Epub 2018 Apr 27.

Authors

Dhika Aditya Gandamana¹, Bin Wang¹, Ciputra Tejo¹, Benoit Bolte², Fabien Gagosz^{2

3}, Shunsuke Chiba¹

Affiliations

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
² Département de Chimie, UMR 7652 and 7653 CNRS, Ecole Polytechnique, 91128, Palaiseau, France.
³ Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, K1N 6N5, Canada.

PMID: 29575429
DOI: 10.1002/anie.201801953

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't