Journal
ORGANIC LETTERS
Volume 22, Issue 17, Pages 6868-6872Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02408
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Funding
- Ministry of Science and Technology of the Republic of China [MOST 107-2628-M-003-001-MY3]
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An efficient method for the direct ss-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.
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