Organotrifluoroborate Preparation, Coupling and Hydrolysis

This book demonstrates a new, simple and etch-free preparation method for organotrifluoroborate salts. It features detailed mechanistic studies that reveal the reactivity of organotrifluoroborate salts in Suzuki-Miyaura coupling reactions.

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.

Nominated as an outstanding Ph.D. thesis by the University of Bristol, UK Includes an extensive review on organotrifluoroborate salts Demonstrates a new, simple and etch-free preparation method for organotrifluoroborate salts Detailed mechanistic studies reveal the reactivity of organotrifluoroborate salts in Suzuki-Miyaura coupling reactions Includes supplementary material: sn.pub/extras

Autorentext
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.

Inhalt
General Introduction.- Organotrifluoroborate Preparation.- Organotrifluoroborate Coupling.- Organotrifluoroborate Hydrolysis.- Conclusions and Future Work.- Experimental: General Experimental Details.- Experimental: Organotrifluoroborate Preparation.- Experimental: Organotrifluoroborate Coupling.- Experimental: Organotrifluoroborate Hydrolysis.