Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones

Mária Bakos; Ádám Gyömöre; Attila Domján; Tibor Soós

doi:10.1002/anie.201700231

Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones

Angew Chem Int Ed Engl. 2017 May 2;56(19):5217-5221. doi: 10.1002/anie.201700231. Epub 2017 Apr 5.

Authors

Mária Bakos¹, Ádám Gyömöre¹, Attila Domján¹, Tibor Soós¹

Affiliation

¹ Research Centre for Natural Sciences, Hungarian Academy of Sciences, Institute of Organic Chemistry, Magyar tudósok körútja 2, 1117, Budapest, Hungary.

PMID: 28378401
DOI: 10.1002/anie.201700231

Abstract

Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H₂ , R-OH or H₂ O generates the required Brønsted acid in a reversible, "turn on" manner. The method is not only a complementary metal-free reductive etherification, but also a niche procedure for ethers that would be either synthetically inconvenient or even intractable to access by alternative synthetic protocols.

Keywords: boranes; catalysis; frustrated Lewis pairs; hydrogenation; reductive etherification.

Publication types

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