Journal
ACS CATALYSIS
Volume 8, Issue 1, Pages 579-583Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03841
Keywords
palladium catalyst; borylation; aryl sulfonium; aryl sulfide; one-pot transformation
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Funding
- JSPS KAKENHI [JP16H01019, JP16H04109, JP16H06887]
- JST ACT-C Grant, Japan [JPMJCR12ZE]
- JSPS
- Grants-in-Aid for Scientific Research [16H01019] Funding Source: KAKEN
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Palladium-catalyzed borylation of aryl sulfonium salts with bis(pinacolato)diboron has been achieved. Because of the sufficient reactivity of aryl sulfoniums and less catalyst-poisonous property of the leaving dialkyl sulfides, the present borylation proceeded under mild reaction conditions. Various functional groups, such as formyl, acetyl, cyano, nitro, and hydroxy groups, were well-tolerated. Aryl sulfoniums were easily prepared from the corresponding aryl sulfides and methyl triflate, and aryl sulfides could be transformed to the corresponding arylboronate esters in one-pot manners. The methylation selectively activated poorer leaving alkylsulfanyl units to culminate in selective borylation over chloro, tosyloxy, and better leaving arylsulfanyl and trifluoromethylsulfanyl units.
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