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Please login to access the full content or check if you have access via2.11.5.4 Method 4: C—C Bond Formation via Polar Reactions of Five-Membered Zirconacycles with Carbon Electrophiles and Related π-Compounds
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Negishi, E.-i.; Takahashi, T., Science of Synthesis, (2003) 2, 761.
As discussed in Section 2.11.4.7.2, the intrinsic nucleophilicity of zirconium—alkyl and zirconium—alkenyl bonds is rather low. Consequently, relatively little is known about the polar reactions of zirconacycles with carbon electrophiles. One significant exception is the chemistry of β,γ-unsaturated five-membered zirconacycles derived from conjugated dienes which may be viewed as bis(allyl)bis(η5-cyclopentadienyl)zirconium derivatives. Their reactions are discussed in Section 2.11.5.4.1. Also noteworthy is the ring-expansion reaction of zirconacyclopentenes with aldehydes to produce seven-membered zirconacycles (Section 2.11.5.4.2). In the 1990s, the reactions of five-membered zirconacycles with allyl ethers have been developed as synthetically useful transformations (Section 2.11.5.4.3). Although still limited, the overall scope of the reactions of zirconacycles with carbon electrophiles is becoming broader.
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