A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes

Jamie H. Docherty, Kieran Nicholson, Andrew P. Dominey, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
Pages (from-to)4686-4691
JournalACS Catalysis
Early online date30 Mar 2020
Publication statusE-pub ahead of print - 30 Mar 2020


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