4.8 Article

Synthesis and Reactivity of a CAAC-Aminoborylene Adduct: A Hetero-Allene or an Organoboron Isoelectronic with Singlet Carbenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 48, Pages 13159-13163

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408371

Keywords

boron; carbine; carbon monoxide; dihydrogen activation; main-group adducts

Funding

  1. NSF [CHE-1359809]
  2. DOE [DE-FG02-13ER16370]
  3. NSERC of Canada
  4. Canada Research Chair
  5. University of Toronto
  6. Direct For Mathematical & Physical Scien
  7. Division Of Chemistry [1359809] Funding Source: National Science Foundation

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A one-electron reduction of a cyclic (alkyl)(amino)carbene (CAAC)-bis(trimethylsilyl)aminodichloroborane adduct leads to a stable aminoboryl radical. A second one-electron reduction gives rise to a CAAC-aminoborylene adduct, which features an allenic structure. However, in manner similar to that of stable electrophilic singlet carbenes, this compound activates small molecules, such as CO and H-2.

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