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

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

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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.

Item Type:
Journal Article
Journal or Publication Title:
ACS Catalysis
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
?? bond-metathesisboraneborondiborylhydroborationcatalysisgeneral chemistry ??
ID Code:
205250
Deposited By:
Deposited On:
27 Sep 2023 10:35
Refereed?:
Yes
Published?:
Published
Last Modified:
16 Jul 2024 00:15