Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 62, Issue 36, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202308563
Keywords
CH Activation; Hydrogen Atom Transfer; Light Alkane; Photocatalysis; Flow Chemistry
Categories
Ask authors/readers for more resources
Despite existing limitations in synthetic methods targeting direct C-H functionalization, a new protocol using photocatalytic hydrogen atom transfer and gaseous carbon monoxide enables the regioselective C-H carbonylation of saturated hydrocarbons. Flow technology is crucial for high gas-liquid mass transfer rates, fast reaction kinetics, scalability, and safety.
Despite their abundance in organic molecules, considerable limitations still exist in synthetic methods that target the direct C-H functionalization at sp(3)-hybridized carbon atoms. This is even more the case for light alkanes, which bear some of the strongest C-H bonds known in Nature, requiring extreme activation conditions that are not tolerant to most organic molecules. To bypass these issues, synthetic chemists rely on prefunctionalized alkyl halides or organometallic coupling partners. However, new synthetic methods that target regioselectively C-H bonds in a variety of different organic scaffolds would be of great added value, not only for the late-stage functionalization of biologically active molecules but also for the catalytic upgrading of cheap and abundant hydrocarbon feedstocks. Here, we describe a general, mild and scalable protocol which enables the direct C(sp(3))-H carbonylation of saturated hydrocarbons, including natural products and light alkanes, using photocatalytic hydrogen atom transfer (HAT) and gaseous carbon monoxide (CO). Flow technology was deemed crucial to enable high gas-liquid mass transfer rates and fast reaction kinetics, needed to outpace deleterious reaction pathways, but also to leverage a scalable and safe process.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available