Mercury in organic chemistry. 20. Alkylation of organomercurials via organocopper reagents

✍ Scribed by R.C. Larock; D.R. Leach

• Book ID: 104234257
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 209 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81925-0

✦ Synopsis

Aryl-, alkenyl-, and alkylmercurials readily cross-couple with primary and secondary alkyl-and alkenylcuprate reagents to provide the first truly general method for the alkylation of a wide variety of organomercurials. Cross-coupling reactions of organometallic reagents have become an increasingly important tool in the formation of carbon-carbon bonds. The ability of organomercurials to accommodate essentially all important organic functional groups, and the ease with which they undergo a variety of mild carbon-carbon bond forming reactions have made organomercurials increasingly attractiveassynthetic intermediates in organic synthesis.' Unfortunately, no general method for the alkylation of organomercurials presently exists. Alkyl halides react with organomercurials only under forcing conditions 2-5 or in the presence of aluminum bromide6 to give low to modest yields of cross-coupled products. We recently reported a convenient