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Synthesis 2021; 53(20): 3777-3790
DOI: 10.1055/a-1513-9968
DOI: 10.1055/a-1513-9968
paper
α-Xanthylmethyl Ketones from α-Diazo ketones
Financial support from Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México (PAPIIT-DGAPA) (Project IN208719) is gratefully acknowledged. P.L.-M. thanks the Consejo Nacional de Ciencia y Tecnología (CONACYT) for a Ph.D. scholarship (No. 308233).
Abstract
A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p-toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.
Key words
xanthates - α-diazo ketones - α-xanthylmethyl ketones - free radicals - nucleophilic substitutionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1513-9968.
- Supporting Information
Publication History
Received: 26 April 2021
Accepted after revision: 20 May 2021
Accepted Manuscript online:
20 May 2021
Article published online:
28 June 2021
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