Di- tert-butyl dicarbonate: a versatile carboxylating reagent

Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di- tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di- tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields. This rea...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (1), p.134-138
Main Authors: Augustine, John Kallikat, Arthoba Naik, Y., Vairaperumal, Veeramani, Narasimhan, Sharmila
Format: Article
Language:English
Subjects:
Aliphatic compounds
Boc-anhydride
Carbon nucleophile
Carboxylating reagent
Chemistry
Di- tert-butyl malonate
Exact sciences and technology
Kinetics and mechanisms
Non-nucleophilic base
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di- tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di- tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields. This reaction represents another useful way to prepare a variety of tert-butyl carboxylates and highlights the synthetic utility of di- tert-butyl dicarbonate as a versatile carboxylating reagent. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.089