Organotrifluoroborate Preparation, Coupling and Hydrolysis

1. Front Matter

   Pages i-xv

   PDF

2. General Introduction

   • Alastair J. J. Lennox

   Pages 1-9

3. Organotrifluoroborate Preparation

   • Alastair J. J. Lennox

   Pages 11-36

4. Organotrifluoroborate Coupling

   • Alastair J. J. Lennox

   Pages 37-80

5. Organotrifluoroborate Hydrolysis

   • Alastair J. J. Lennox

   Pages 81-131

6. Conclusions and Future work

   • Alastair J. J. Lennox

   Pages 133-146

7. Experimental

   • Alastair J. J. Lennox

   Pages 147-223

Alistair Lennox's thesis reports on the reactivity of organotrifluoroborates, which are becoming increasingly important reagents in synthesis. The thesis is divided into three sections. The first section describes a method for preparing organotrifluoroborates. The second section reports on a mechanistic investigation into the main application of RBF3K reagents as coupling partners in Suzuki-Miyaura coupling, phenomena identified as arising from organotrifluoroborate hydrolysis and fluoride release. The final section reports on a detailed investigation into the hydrolysis mechanism, a prerequisite for their Suzuki-Miyaura coupling, and how it may be predicted and controlled. This research has uncovered many interesting and useful details and shows how problems associated with Suzuki-Miyaura coupling can best be addressed. There has already been wide industrial uptake of the new procedures and insights. The broad nature and clear and succinct style will make the thesis a valuable resource for anyone working in synthesis, organometallic chemistry, or in homogeneous catalysis.

• Cross-coupling
• Glassware Etching
• Kinetics of Hydrolysis
• Organotrifluoroborate Salts
• Side-product Suppression
• Suzuki-Miyaura Coupling Mechanism
• Trifluoroborate Reactivity
• Trifluoroborates

• School of Chemistry, University of Bristol, Bristol, United Kingdom

  Alastair J. J. Lennox

Dr. Lennox grew up in York, received his undergraduate degree from the University of Manchester and his PhD from the University of Bristol. His interests lie in organic reaction mechanisms, of which his PhD thesis was focussed and the subject of a book he is currently co-writing.

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