期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 7, 页码 1720-1725出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705577
关键词
glycerol; green chemistry; nitriles; organolithium reagents; water
资金
- MINECO of Spain [CTQ2014-51912-REDC, CTQ2016-75986-P]
- Gobierno del Principado de Asturias [GRUPIN14-006]
- Fundacion BBVA
- EPSRC [EP/N011384/1]
- Society of Spanish Researchers in the UK (SRUK)
- Fundacion Santander
- Scottish Funding Council
- EPSRC [EP/N011384/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1687703, EP/N011384/1] Funding Source: researchfish
Edging closer towards developing air and moisture compatible polar organometallic chemistry, the chemoselective and ultrafast addition of a range of aryllithium reagents to nitriles has been accomplished by using glycerol as a solvent, at ambient temperature in the presence of air, establishing a novel sustainable access to aromatic ketones. Addition reactions occur heterogeneously (on glycerol conditions), where the lack of solubility of the nitriles in glycerol and the ability of the latter to form strong intermolecular hydrogen bonds seem key to favouring nucleophilic addition over competitive hydrolysis. Remarkably, PhLi exhibits a greater resistance to hydrolysis working on glycerol conditions than on water. Introducing glycerol as a new solvent in organolithium chemistry unlocks a myriad of opportunities for developing more sustainable, air and moisture tolerant main-group-metal-mediated organic synthesis.
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