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Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source

2021; Nature Portfolio; Volume: 13; Issue: 2 Linguagem: Inglês

10.1038/s41557-020-00621-x

1755-4349

Yong Ho Lee, Elliott H. Denton, Bill Morandi,

Organoboron and organosilicon chemistry

Hydroformylation, a reaction that installs both a C-H bond and an aldehyde group across an unsaturated substrate, is one of the most important catalytic reactions in both industry and academia. Given the synthetic importance of creating new C-C bonds, 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 palladium-catalysed strategy that uses 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. An extension of this protocol to four chemodivergent carbonylations further highlights the creative opportunity offered by this strategy in carbonylation chemistry.