4.8 Article

Intramolecular Aminoboration of Unfunctionalized Olefins

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 43, Pages 12636-12639

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505489

Keywords

aminoboration; boronic acids; boronic esters; Suzuki cross-coupling; synthetic methods

Funding

  1. National Natural Science Foundation of China [NSFC 20972072, NSFC 21272121]

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A direct and catalyst-free method for the intramolecular aminoboration of unfunctionalized olefins is reported. In the presence of BCl3 (1 equiv) as the sole boron source, intramolecular aminoboration of sulfonamide derivatives of 4-penten-1-amines, 5-hexen-1-amines, and 2-allylanilines proceeded readily without the use of any catalyst. The boronic acids obtained after hydrolysis could be converted into the corresponding pinacol borates in a straightforwardmanner by treatment with pinacol under anhydrous conditions.

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