Copper-Catalyzed Asymmetric Borylacylation of Styrene and Indene Derivatives

The enantioselective copper-catalyzed borylacylation of aryl olefins with acyl chlorides and bis-(pinacolato)­diboron is reported. This three-component reaction involves an enantioselective syn-borylcupration of the aryl olefin, followed by a nucleophilic attack on the acyl chloride. This reaction p...

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Veröffentlicht in:Journal of organic chemistry 2021-03, Vol.86 (6), p.4616-4624
Hauptverfasser: Yang, Zhen, Li, Peiyuan, Lu, Hongjian, Li, Guigen
Format: Artikel
Sprache:eng
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Zusammenfassung:The enantioselective copper-catalyzed borylacylation of aryl olefins with acyl chlorides and bis-(pinacolato)­diboron is reported. This three-component reaction involves an enantioselective syn-borylcupration of the aryl olefin, followed by a nucleophilic attack on the acyl chloride. This reaction proceeds with a 2 mol % catalyst loading and is generally completed within 30 min at room temperature. Because the boron moiety can be converted into versatile functional groups and the carbonyl group is a ubiquitous functional group, the resulting chiral β-borylated ketones are versatile intermediates in organic synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00031