Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 32, Pages 7212-7218Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000549
Keywords
alkenylation; B-H activation; carboranes; catalysis; transition metals
Categories
Funding
- National Natural Science Foundation of China [21772223]
- Science and Technology Commission of Shanghai Municipality [18590760800]
- China Postdoctoral Science Foundation [BX20180341]
- Shanghai Post-doctoral Excellence Program [2018027]
- Hong Kong Research Grants Council [14305017, N CUHK402/18]
- Chinese Academy of Sciences
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Iridium-catalyzed formal alkyne hydroboration with cage B-H of o-carborane has been achieved, leading to the controlled synthesis of a series of 3,6-[trans-(AlkCH=CH)](2)-o-carboranes (Alk=alkyl), 3-cis-(ArCH=CH)-o-carboranes (Ar=aryl), and 3-cis-(ArCH=CH)-6-trans-(AlkCH=CH)-o-carboranes in high yields with excellent regio- and very good cis-trans selectivity. The most electron-deficient B(3,6)-H vertices favor oxidative addition on electron-rich metal centers, which is responsible for the regioselectivity. On the other hand, the configuration of the resultant olefinic units is dominated by alkyne substituents. Alkyl groups lead to a trans-configuration whereas bulky aryl substitutions result in cis-configuration.
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