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

preprint
submitted on 06.02.2020 and posted on 07.02.2020 by Jamie Docherty, Kieran Nicholson, Andrew P Dominey, Stephen Thomas
9-Borabicyclo[3.3.1]nonane (H-B-9-BBN) has been used as a catalyst for the sequential double hydroboration of alkynes with pinacolborane (HBpin) to give alkyl gem-di-pinacol boronic esters. 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 labelling experiments are indicative of an σ-bond metathesis exchange pathway.

History

Email Address of Submitting Author

stephen.thomas@ed.ac.uk

Institution

University of Edinburgh

Country

UK

ORCID For Submitting Author

0000-0001-8614-2947

Declaration of Conflict of Interest

None

Exports