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Title: Main group species for catalytic hydroboration
Author: Bismuto, Alessandro
ISNI:       0000 0004 7429 7935
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2018
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Modern synthetic chemistry is unimaginable without transition metal catalysis. Yet the often high cost, toxicity and scarcity of many transition metals is driving attempts to find sustainable alternatives. Thus, the development of catalytic processes using main-group catalysts is now of broad interest. This thesis reports the development of a facile protocol for the aluminium-catalysed hydroboration of alkynes, alkenes and polar bonds using commercially-available catalysts. The catalytic hydroboration is proposed to occur by hydroalumination followed by product release through σ-bond metathesis with pinacol borane. An alternative route to alkenyl boranes is the 1,1-carboboration of alkynes using stoichiometric B(C6F5)3. A zwitterionic intermediate in the Piers' borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3 has been characterised and its divergent reactivity identified. This has led to the development of a B(C6F5)3 - catalysed hydroboration of alkynes using HBpin.
Supervisor: Thomas, Stephen ; Cowley, Michael ; Schneider, Uwe Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: catalysis ; aluminium catalysts ; functionalised alkenes