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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 19
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Original Articles

B(C6F5)3-catalyzed synthesis of benzylic azides

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Pages 1771-1776 | Received 27 Jun 2017, Published online: 31 Aug 2017
 

ABSTRACT

B(C6F5)3 was found to catalyze the reaction between trimethylsilyl azide and benzylic acetates. Secondary and tertiary benzylic acetates were competent substrates in this reaction providing the azide products in moderate to high yields. Mechanistic experiments are consistent with the possible formation of a Lewis acid-base pair between the B(C6F5)3 and trimethylsilyl azide.

GRAPHICAL ABSTRACT

Additional information

Funding

The College of Charleston is acknowledged for financial support. The NMR spectrometer at the College of Charleston is supported by the National Science Foundation under Grant No. 1429308.

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