Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant. Issue 6 (20th April 2015)

• Record Type: Journal Article
• Authors: Tobisu, Mamoru; Morioka, Toshifumi; Ohtsuki, Akimichi; Chatani, Naoto
• Is Part Of: Chemical science. Volume 6:Issue 6(2015:Jun.)
• Page Start: 3410
• Page End: 3414
• Publication Date: 2015-04-20
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc00305a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A nickel catalyst for reductive cleavage of aryl ethers in the absence of an external reductant is developed. The alkoxy group of the substrate serves as an internal reductant. Abstract : The reductive cleavage of the C–O bonds of aryl ethers has great potential in organic synthesis. Although several catalysts that can promote the reductive cleavage of aryl ethers have been reported, all such systems require the use of an external reductant, e.g., hydrosilane or hydrogen. Here, we report the development of a new nickel-based catalytic system that can cleave the C–O bonds of ethers in the absence of an external reductant. The hydrogen atom required in this new reductive cleavage reaction is provided by the alkoxy group of the substrate, which serves as an internal reductant. The absence of an external reductant enables the unique chemoselectivity, i.e., the selective reduction of an alkoxy group over alkenes and ketones.