5 years ago

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

Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones
Tibor Soós, Attila Domján, Mária Bakos, Ádám Gyömöre
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 H2O 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. Double success: A metal-free reductive etherification method using frustrated-Lewis-pair-promoted reduction reactions of carbonyl compounds was developed. The key to success was the deliberate application of recently discovered water-tolerant frustrated Lewis pairs. The developments can be viewed as a double success in FLP catalysis and formation of ether bonds.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700231

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