Heteroatom-containing aryl iodides

Heteroatom-containing aryl iodides react with 1,3-dienes in the presence of a palladium catalyst and an appropriate base to afford a variety of oxygen and nitrogen heterocycles. Mechanistically, heteroannulation proceeds via aryl-and TC-aUylpaUadium intermediates. Similar results have been obtained using either Pd(OAc)2 or Pd(dba)2 as catalysts (Scheme 29). The yield of... 

Besides the preparation of macrocycles, cyclizations to give heteroatom-containing five-, six-, and seven-membered rings have been investigated [211, 595-599]. Thus, the construction of indoles, benzofurans, dihydroisoquinoHnes, and benzazepines has been reported. Starting from aryl iodides with appropriate... 

Catellani [61] reported a palladium/norbomene-catalyzed synthesis of heteroatom-containing o-teraryls from aryl iodides and heteroarenes (including indoles and pyrroles) through double C-H arylation. Fagnou s group [62] applied their own protocol (Pd(II)/Ag(I)/carboxylic acid) to achieve the direct arylation of azaindoles. Itami [63] demonstrated the first iridium-catalyzed C-H arylation of heteroarenes (involving indoles and pyrroles) with aryl halides. 

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