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Pd-Catalyzed Selective Addition of Heteroaromatic C−H Bonds to C−C Triple Bonds under Mild Conditions

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journal contribution
posted on 22.08.2000, 00:00 by Wenjun Lu, Chengguo Jia, Tsugio Kitamura, Yuzo Fujiwara
Simple heteroarenes such as pyrroles and indoles undergo addition reactions to C−C triple bonds in the presence of a catalytic amount of Pd(OAc)2 under very mild conditions, affording cis-heteroarylalkenes in most cases. The cleavage of aromatic C−H bonds is the possible rate-determining step in CH2Cl2, and the addition of heteroaromatic C−H bonds to C−C triple bonds is in a trans-fashion.