title: Organotrifluoroborates: Another Branch of the Mighty Oak.
abstract: Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules. Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure. Currently >600 structurally diverse reagents of this class are commercially available, and >850 such compounds have been reported from the author's laboratory. The organotrifluoroborates can be utilized as shelf-stable precursors to a variety of end products through simple functional group transformations and have also been employed as partners in cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or individual formats. Within the realm of cross-coupling reactions, organotrifluoroborates provide a practical entry to substructural entities not readily accessed using other organometallic reagents, and most recently, the development of a novel mechanistic paradigm for cross-coupling promises to expand the range of accessible cross-coupling partners even further to include both single- and two-electron processes.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander