Cp(*)RuCl-catalyzed formal intermolecular cyclotrimerization of three unsymmetrical alkynes through a boron temporary tether: regioselective four-component coupling synthesis of phthalides |
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Authors: | Yamamoto Yoshihiko Ishii Jun-Ichi Nishiyama Hisao Itoh Kenji |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan. yamamoto@apchem.nagoya-u.ac.jp |
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Abstract: | 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. |
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