Heteroaromatic compounds coupling with alkenes

The CDC reaction of arenes and alkenes can be applied to heteroaromatic compounds. Coupling with furan, thiophene, pyrrole, benzofuran. 

On the other hand, the direct arylation of carbanionic species generated from substrates having relatively acidic hydrogens such as active methylene compounds and ketones can occur (mechanism B) [5,6]. Aryl halides are also capable of coupling directly with appropriately functionalized aromatic substrates and five-membered heteroaromatic compounds as formal carbon nucleophiles via cleavage of their unactivated C-H bonds [5,7-9]. The Fujiwra-Moritani reaction, which is the arylation of alkenes with arenes, is also useful for preparing arylalkenes without employing any halides (mechanism D) [10,11]. 

Satoh, M. Miyaura, N. Suzuki, A. 1987. Palladium catalyzed cross-coupling reaction of (1-ethoxy-l-alken-2-yl)boranes with ortho-functionalized iodoarenes. A novel and convenient synthesis of benzo fused heteroaromatic compounds. Synthesis 373-377. 

Heteroaromatic compounds show similar behavior to benzene derivatives. Furan, pyrrole, thiophene, benzofuran, indole, benzothiophene, and their related compounds undergo CDC reactions with alkenes. In the case of furan, the coupling reactions with acrylates, acrylonitrile, styrenes, and... 

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