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2017•Synthetic CommunicationsRequires access

B(C6F5)3-catalyzed synthesis of benzylic azides

Michael S. Wrigley, Timothy J. Barker

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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.

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What this paper is about

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.

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Available 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.

Key concepts: Trimethylsilyl azide, Chemistry, Azide, Lewis acids and bases, Trimethylsilyl, Catalysis, Base (topology), Medicinal chemistry

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