Deoxygenative functionalization of alcohols, ethers, and carbonyl compounds by chromium catalysis
In the authors' words
The development of an efficient and unified methodology for converting ubiquitous alcohols, ethers, carbonyls, and esters into value-added products via the activation of C-O single and double bonds is of great interest and importance but remains a challenging goal. Herein, we report an efficient and general chromium-catalyzed strategy for the deoxygenative functionalization of alcohols, ethers, and carbonyl compounds with a number of electrophiles. This general strategy couples these oxygenated functional groups with a number of electrophiles, providing an efficient route for the synthesis of a broad range of synthetically appealing organosilicon, organogermanium, organostannane, and organoboron compounds. Moreover, this chromium-catalyzed strategy is demonstrated to be readily scalable and applicable to the late-stage functionalization of various biorelevant molecules. Mechanistic investigations suggest that this deoxygenative functionalization was initiated by two-electron oxidative addition of the C-O bond to a highly active, low-valent chromium species, generating an organochromium intermediate that reacts with a number of electrophiles to construct C-Si, C-Ge, C-Sn, and C-B bonds.
Appeared: Sunday, September 27. Science Advances. Peer-reviewed journal.