Pd-catalyzed selective addition of heteroaromatic C-H bonds to C-C triple bonds under mild conditions.
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 CH(2)Cl(2), and the addition of heteroaromatic C-H bonds to C-C triple bonds is in a trans-fashion.
Lu
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Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fukuoka, 812-858, Japan.
Jia
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C
Kitamura
T
T
Fujiwara
Y
Y
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry
D005663:Furans; D006571:Heterocyclic Compounds; D007211:Indoles; D009942:Organometallic Compounds; D011758:Pyrroles; C008261:lead acetate