4.8 Article

Synthesis of Cyclic Amine Boranes through Triazole-Gold( I)Catalyzed Alkyne Hydroboration**

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 21, Pages 5418-5422

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402614

Keywords

alkynes; cyclization; boranes; gold; synthetic methods

Funding

  1. NSF [CHE-0844602, CHE-1228336]
  2. NSFC [21228204]
  3. Division Of Chemistry
  4. Direct For Mathematical & Physical Scien [0844602, 1228336] Funding Source: National Science Foundation

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The first catalytic alkyne hydroboration of propargyl amine boranecarbonitriles is accomplished with triazole-Au-I complexes. While the typical [L-Au](+) species decomposes within minutes upon addition of amine boranecarbonitriles, the triazole-modified gold catalysts (TA-Au) remained active, and allowed the synthesis of 1,2-BN-cyclopentenes in one step with good to excellent yields. With good substrate tolerability and mild reaction conditions (open-flask), this new method provides an alternative route to reach the interesting cyclic amine borane with high efficiency.

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