Cp*RuCl-catalyzed formal intermolecular cyclotrimerization of three unsymmetrical alkynes through a boron temporary tether: Regioselective four-component coupling synthesis of phthalides

被引:148
作者
Yamamoto, Y [1 ]
Ishii, J [1 ]
Nishiyama, H [1 ]
Itoh, K [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1021/ja051377d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly substituted phthalides were efficiently synthesized by sequential Cp*RuCl-catalyzed cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes and palladium(II)-catalyzed carbonylation of the resultant arylboronates. The intermediate arylboronate was isolated and unambiguously characterized by X-ray crystallography. The perfect regioselectivity of the ruthenium-catalyzed formal intermolecular cyclotrimerization was discussed on the basis of the density functional calculations of a boraruthenacycle intermediate.
引用
收藏
页码:9625 / 9631
页数:7
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