Naphthalenes, isoquinolines, and a benzazocine from zirconocene - Copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes

被引:28
作者
Ramakrishna, TVV [1 ]
Sharp, PR [1 ]
机构
[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA
关键词
D O I
10.1021/ol034040u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Commercially available 1-bromobenzocyclobutene is a potentially useful synthon particularly with the application of organometallic methodology. Here we show that it is readily converted into Cp2Zr(benzocyclobutadiene), which couples with alkynes or nitriles giving five-membered zirconacycles. Treatment of these alkyne- or nitrile-derived zirconacycles with CuCl yields substituted naphthalenes, isoquinolines, or in the presence of MeO2C-CC-CO2Me, a 2-benzazocine containing an eight-membered ring.
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页码:877 / 879
页数:3
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