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Synfacts 2009(2): 0201-0201  
DOI: 10.1055/s-0028-1087646
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Di-tert-butyl Dicarbonate: A Versatile Carboxylating Agent

Contributor(s): Paul Knochel, Andrei Gavryushin
J. K. Augustine*, Y. A. Naik, V. Vairaperumal, S. Narasimhan
Syngene International Ltd., Bangalore and Kuvempu University, Shimoga, India
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Carbanions, generated by metalation of suitable arenes or alkylarenes with LDA, can be efficiently trapped by di-(tert-butyl) dicarbonate, leading to the corresponding tert-butyl (hetero)aryl carboxylates, tert-butyl acetates or unsymmetrical malonates in high yields. This versatile method affords a direct and convenient way of carboxylation of various carbanions to obtain stable tert-butyl esters of high synthetic utility ­using a simple and robust synthetic protocol.