Organic Letters
Organic Letters
4 years ago

Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides

Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides
Ekta Gupta, Kishor Mohanan, Ruchir Kant
An efficient, metal-free decarbethoxylative arylation protocol for the synthesis of α-aryl-α-fluoroamides from fluoromalonamates, under ambient reaction conditions using aryne as an electrophilic arylating agent, is reported. This decarbethoxylative arylation proceeds under mild conditions and provides a practical and effective entry to a wide range of α-aryl-α-fluoroacetamides. Interestingly, the use of the tert-butyl ester of fluoromalonamate prevented the otherwise rapid decarboxylation step, affording the arylated fluoromalonamate in moderate yield.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03072

DOI: 10.1021/acs.orglett.7b03072

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