9-Borabicyclo[3.3.1]nonane dimer (CAS 21205-91-4)

9-Borabicyclo[3.3.1]nonane dimer, often abbreviated as 9-BBN dimer, is a prominent organoborane compound widely utilized in organic synthesis for its unique ability to selectively hydroborate alkenes, thereby converting them into organoboron compounds which can further undergo a variety of transformations. This dimeric structure consists of two 9-borabicyclo[3.3.1]nonane units connected through a boron-boron bond, a feature that significantly stabilizes the molecule and enhances its reactivity. The mechanism of action of 9-Borabicyclo[3.3.1]nonane dimer involves the formation of a complex with alkenes, facilitating the addition of the boron atom across the carbon-carbon double bond in a highly regioselective manner. This regioselectivity is particularly valuable in research for the synthesis of complex organic molecules, as it allows for precise control over the formation of products. Additionally, the hydroboration reaction mediated by 9-Borabicyclo[3.3.1]nonane dimer is stereospecific, typically yielding cis-addition products, which can be subsequently converted into a wide range of functional groups through reactions such as oxidation or Suzuki coupling. The versatility and control offered by 9-Borabicyclo[3.3.1]nonane dimer make it an indispensable tool in the development of new synthetic methodologies, playing a pivotal role in the construction of molecules for research applications across chemistry and materials science.