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Visible light-mediated formal alkylation and [4+1]-cycloaddition strategies of silyl enol ethers with aryldiazoacetates

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Author(s):
Cariello, Guilherme ; Gallo, Rafael D. C. ; Deflon, Victor M. ; Cormanich, Rodrigo A. ; Jurberg, Igor D.
Total Authors: 5
Document type: Journal article
Source: CHEMICAL COMMUNICATIONS; v. 61, n. 10, p. 5-pg., 2024-12-03.
Abstract

A reaction sequence of visible light-mediated cyclopropanation/acid-promoted ring-opening is described for the formal alkylation of silyl enol ethers with aryldiazoacetates. Under the same conditions, the Danishefsky's diene can react with aryldiazoacetates to afford [4+1]-cycloaddition adducts. Key mechanistic aspects are proposed based on experimental evidence and DFT calculations. (AU)

FAPESP's process: 22/01104-3 - Photochemistry with visible light aiming at the mild formation of carbenes and nitrenes as versatile intermediates for the functionalization of organic molecules
Grantee:Igor Dias Jurberg
Support Opportunities: Regular Research Grants
FAPESP's process: 22/16188-8 - Computational and experimental studies of hydrogen bonding involving organic F atoms as acceptors
Grantee:Guilherme Cariello Silva
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 20/00144-6 - Structural proteomics: design, synthesis and application of new generation crosslinking agents
Grantee:Rafael Douglas Clemente Gallo
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches
Grantee:Rodrigo Antonio Cormanich
Support Opportunities: Research Grants - Young Investigators Grants