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| - New Method for Preparation of Coumarins and Quinolinones viaPd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds
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| - A new and general method has been developed for preparation of coumarins and quinolinones byintramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fastintramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)2 ina mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones inmoderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodologyproved to tolerate a number of functional groups such as Br and CHO. On the basis of isotopeexperiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalationof aromatic C−H bonds by in-situ generated cationic Pd(II) species has been discussed. Also theinvolvement of vinylcationic species has been suggested.
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