Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 5, Pages 1970-1974Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909655
Keywords
boron; carbocycles; cross-coupling; silicon; small ring systems
Categories
Funding
- JSPS [17H05430]
- JSPS KAKENHI [19K23621, 17H06173]
- Nagase Science and Technology Foundation
- Sumitomo Foundation
- HOKUSAI GreatWave (RIKEN) [G19012]
- Grants-in-Aid for Scientific Research [19K23621] Funding Source: KAKEN
Ask authors/readers for more resources
The silaboration of [1.1.1]propellane enables direct introduction of B and Si functional groups onto the bicyclo[1.1.1]pentane (BCP) scaffold in high yield under mild, additive-free conditions. The silaborated BCP can be obtained on a gram-scale in a single step without the need for column-chromatographic purification, and is storable and easy to handle, providing a versatile synthetic intermediate for BCP derivatives. We also describe various conversions of the C-B/C-Si bonds on the BCP scaffold, including development of a modified Suzuki-Miyaura cross-coupling reaction at the highly sterically hindered bridgehead sp(3) carbon center of the BCP skeleton using a combination of highly activated BCP boronic esters, copper(I) oxide, and a PdCl2(dppf) catalyst system.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available