Synthesis of 2-acyl-1,4-diketones via the diacylation of {alpha},{beta}-unsaturated ketones

Journal Article · Mon Aug 17 00:00:00 EDT 1998 · Organometallics

DOI:https://doi.org/10.1021/om980303q· OSTI ID:655376

Li, N S; Yu, S; Kabalka, G W ^[1]

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1. Univ. of Tennessee, Knoxville, TN (United States)

The first example of a diacylation of the carbon-carbon double bond in {alpha},{beta}-unsaturated ketones is described. The reaction of acylcyanocuprate reagents with {alpha},{beta}-unsaturated ketones, followed by C-acylation, produces 2-acyl-1,4-diketones in good yields (50--89%). The 1,4-addition of organocuprate reagents to conjugated enones, followed by trapping of the enolate intermediates with various electrophiles, is one of the most useful synthetic reactions. However, to the best of the authors` knowledge, 1,4-acylation followed by trapping of the enolate intermediates with acid chloride has not been reported.

• Sponsoring Organization: USDOE, Washington, DC (United States)
• OSTI ID: 655376
• Journal Information: Organometallics, Journal Name: Organometallics Journal Issue: 17 Vol. 17; ISSN 0276-7333; ISSN ORGND7
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
ACYL RADICALS
CHEMICAL BONDS
CHEMICAL REACTIONS
CUPRATES
CYANIDES
KETONES
SYNTHESIS