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Palladium-Catalyzed Carboformylation Enabled by a Molecular Shuffling Process

preprint
submitted on 08.07.2020 and posted on 09.07.2020 by Yong Ho Lee, Elliott Denton, Bill Morandi

Hydroformylation, a reaction which installs both a C–H bond and an aldehyde group across an unsaturated substrate, is one of the most important catalytic reactions both in industry and academia. Given the synthetic importance of creating new C–C bonds, and the widespread academic and industrial impact of hydroformylation, the development of carboformylation reactions, wherein a new C–C bond is formed instead of a C–H bond, would bear enormous synthetic potential to rapidly increase molecular complexity in the synthesis of valuable aldehydes. However, the demanding complexity inherent in a four-component reaction, utilizing an exogenous CO source, has made the development of a direct carboformylation reaction a formidable challenge. Here, we describe a molecular shuffling strategy featuring the use of readily available aroyl chlorides as a carbon electrophile and CO source, in tandem with a sterically congested hydrosilane, to perform a stereoselective carboformylation of alkynes under palladium catalysis. An extension of this protocol to four chemodivergent carbonylations further highlights the creative opportunity offered by this molecular shuffling strategy in carbonylation chemistry.

Funding

Horizon 2020 - ERC Shuttle Cat, Project ID: 757608

LG Chem (fellowship to Y.H.L.)

ETH Zürich

History

Email Address of Submitting Author

morandib@ethz.ch

Institution

ETH Zürich

Country

Switzerland

ORCID For Submitting Author

0000-0003-3968-1424

Declaration of Conflict of Interest

No conflict of interest

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