By A. Furstner
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Additional resources for Active Metals [chemistry]
Wc have recently developed a direct synthetic method for the one-pot synthcsis of lactones, spirolactones, di-spirolactones, tertiary alcohols, and even 1,2-diols from the corresponding conjugated diene-magnesium reagents mediated by Rieke magnesium 1361. The overall lactonization procedure can be considered as a molecular assembling process in which three distinct individual species, a conjugated dienc, a ketone, and carbon dioxide, are used to build a complex organic molecule in a well-controlled manner.
In conjunction, it is also an important route to many substituted 1,3-dienes. Table 1-18 shows coupling reactions of organozinc and aryl and vinyl halides. It should be noted that organozinc reagents can also be transmetallated to nickel, allowing for the full range of chemistry available to that metal as well. 7 Intramolecular Cyclizations and Conjugate Additions Mediated by Rieke Zinc Rieke zinc is superior to other forms of activated zinc when applied to intramolecular cyclizations and conjugate additions.
However, ordinary copper metal is not sufficiently reactive to add oxidatively to organic halides. This is evidenced by the Ullman biaryl synthesis which involves the reaction of copper bronze with aryl iodides to form biaryl compounds 1681. Typically, these reactions are carried out in sealed tubes at temperatures of 100 to 300 "C for long periods of time ranging from hours to days. Of much more synthetic utility are the organocopper, lithium di-organocuprate, and various hcterocupratc reagents developcd over the past few years.
Active Metals [chemistry] by A. Furstner