Abstract

The use of organometallic reagents in organic synthesis had its beginning around 1900 when Victor Grignard discovered that alkyl and aryl halides react with magnesium metal to give homogeneous solutions containing organomagnesium compounds. The “Grignard reagents” proved to be highly reactive carbon nucleophiles and have remained very useful synthetic reagents since that time. Organolithium reagents came into synthetic use somewhat later. This chapter will focus primarily on Grignard reagents and organolithium compounds. These reagents are highly reactive carbon nucleophiles with fundamental applications in organic synthesis. We will also consider zinc, cadmium, mercury, indium, and lanthanide organometallics. Each of these classes of compounds has more specialized places in synthetic methodology. Certain of the transition metals, such as copper, palladium, and nickel, are important in synthetic methodology and will be discussed in Chapter 8.

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