期刊
ACS CATALYSIS
卷 11, 期 24, 页码 14803-14810出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03731
关键词
mechanochemistry; cross-coupling; polyfluoroarylation; ball mill; synthesis
资金
- Japan Society for the Promotion of Science (JSPS) via KAKENHI [18H03907, 17H06370, 20H04795, 21H019260]
- JST via CREST [JPMJCR19R1]
- FOREST Grant [PJ2521A02I]
- Institute for Chemical Reaction Design and Discovery (ICReDD)
- Grants-in-Aid for Scientific Research [18H03907, 17H06370, 20H04795] Funding Source: KAKEN
The palladium-catalyzed cross-coupling under solid-state high temperature ball-milling conditions enables efficient construction of polyfluorinated structural motifs without the need for stoichiometric additives, large amounts of organic solvents, and exhibits a broad substrate scope.
The Suzuki-Miyaura cross-coupling between poly-fluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with this transformation involves the slow transmetalation with weakly nucleophilic polyfluorinated organoboron reagents, which often reduces the yield of the coupling products. Here, we show that solid-state high-temperature ball-milling conditions facilitate a palladium-catalyzed cross-coupling with polyfluorinated arylboronic acids and pinacol esters employing a simple catalytic system in the absence of any stoichiometric additives. This reaction exhibits a broad substrate scope and can be carried out in air, and the use of large amounts of dry and degassed organic solvents is not required. The successful cross-coupling of weakly nucleophilic polyfluorinated organoboron reagents was ascribed to the extremely high concentrations of the substrates and the catalyst under solid-state conditions.
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