期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 22, 页码 7125-7132出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201300443
关键词
allenes; copper; dienes; hydroboration; ligand effects
资金
- MEXT, Japan
- Mitsubishi Foundation
- JSPS
- Grants-in-Aid for Scientific Research [25105731, 25708017, 11J03004] Funding Source: KAKEN
The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-sigma-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes.
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