Docherty, Jamie H. and Nicholson, Kieran and Dominey, Andrew P. and Thomas, Stephen P. (2020) A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes. ACS Catalysis, 10 (8). pp. 4686-4691. ISSN 2155-5435
Full text not available from this repository.Abstract
Olefin hydroboration reactions provide efficient access to synthetically versatile and easily handled organoboronic esters. In this study, we demonstrate that the commercially available organoborane reagent 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) can serve as a catalyst for the sequential double hydroboration of alkynes using pinacolborane (HBpin). This strategy, which is effective for a wide range of terminal alkynes, is predicated upon a key C(sp3)-B/B-H transborylation reaction. Transition-state thermodynamic parameters and 10-boron-isotopic labeling experiments are indicative of a σ-bond metathesis exchange pathway.