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Synthesis 2021; 53(23): 4409-4418
DOI: 10.1055/a-1549-1082
DOI: 10.1055/a-1549-1082
feature
Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation
The authors thank the Ministry of Science and Technology, Republic of China (MOST 107-2628-M-003-001-MY3) for financial support.
Abstract
We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under mild, metal-free conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/rearrangement sequence. Mechanistic investigations revealed that C–O bond cleavage on a possible betaine intermediate is the key step for the installation of the keto-functionality at the β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by a scale-up reaction and synthetic transformations of the products.
Key words
β-acylation - functionalized 2-ylideneoxindoles - indolin-3-ones - phospha-Michael addition - phosphine catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1549-1082.
- Supporting Information
Publication History
Received: 17 June 2021
Accepted after revision: 13 July 2021
Accepted Manuscript online:
13 July 2021
Article published online:
16 August 2021
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