In most Suzuki-Miyaura carbon-carbon cross-coupling reactions, the borabicyclo[3.3.1]nonane scaffold (9-BBN) only serves as an auxiliary facilitating the transmetalation step and thus is transformed into by-products. There are rare examples where the 9-BBN derivatives serve as the potentially diverse C8 building blocks in cross-coupling reactions. Herein, we report a cobalt-catalyzed migratory carbon-carbon cross-coupling reaction of the in situ formed 9-BBN ate complexes to afford diverse aryl- and alkyl-functionalized cyclooctenes. Preliminary mechanistic studies suggest the oxidation-induced cis-bicyclo[3.3.0]oct-1-ylborane is the key intermediate in this migratory cross-coupling reaction, which promotes the development of other diverse migratory cross-coupling of borate complexes.

https://www.sciencedirect.com/science/article/pii/S1001841724005710