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Synthesis 2018; 50(10): 2033-2040
DOI: 10.1055/s-0036-1591545
DOI: 10.1055/s-0036-1591545
paper
Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane
We thank the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Mahidol University under the National Research Universities Initiative, Thailand Research Fund (IRN58W0005), Swedish Research Council through the Swedish Research Links Programme in collaboration with Professor Pher G. Andersson, Stockholm University, Sweden (2013-6744), CNRS-PICS Program through collaboration with Professor Fabien Gagosz, École Polytechnique, France (PICS 6663), and the Franco–Thai Cooperation Program in Higher Education and Research (PHC-Siam 2017) for financial support. C.K. also thanks the Thailand Toray Science Foundation for Science and Technology Research Grants.Further Information
Publication History
Received: 18 January 2018
Accepted after revision: 25 January 2018
Publication Date:
07 March 2018 (online)
Abstract
Difluoro(phenylsulfanyl)methane (PhSCF2H) was found to undergo a reaction with aromatic compounds mediated by SnCl4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S,S′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.
Key words
electrophilic formylation - thionium cation - aldehydes - electrophilic addition - carbocationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591545.
- Supporting Information
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