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

Yong Ho Lee, Elliott H. Denton, Bill Morandi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

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. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)123-130
Number of pages8
JournalNature Chemistry
Volume13
Issue number2
DOIs
Publication statusPublished - 2021 Feb
Externally publishedYes

Bibliographical note

Funding Information:
We acknowledge ETH Zurich, the European Research Council under the European Union’s Horizon 2020 research and innovation programme (Shuttle Cat, project ID 757608) and LG Chem (fellowship to Y.H.L.) for financial support. We thank the NMR, MS (MoBiAS) and X-ray (SMoCC) service departments at ETH Zurich for technical assistance.

Publisher Copyright:
© 2021, The Author(s), under exclusive licence to Springer Nature Limited.

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

Fingerprint

Dive into the research topics of 'Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source'. Together they form a unique fingerprint.

Cite this