Tandem coupling-cyclization applications

The first high yielding one-pot tandem Hartwig-Buchwald-Heck cyclization was reported and applied to the synthesis of 2,3-disubstituted indoles [201]. Commercially available enone 123 was coupled with 1,2-dibromobenzene to provide A -arylcncaminonc 124 which subsequently cyclized to indole derivative 125 [201]. This reaction was widely applicable to a variety of electron rich, electron poor and neutral aromatic bromides and chlorides as well as heterocyclic halides. Excellent yields were obtained regardless of the substitution pattern on the aromatic halide. 

Pyrrolo[2,1,5-cd]indolizines and porphyrins It has recently been found that McMurry coupling opens an efficient route for the preparation of pyrrolo[2,l,5-cdjindolizines 101 and other substituted derivatives, by intramolecular reductive condensation of 3,5-diacylindolizines [139] (Figure 6.18). Another application of the McMurry reaction in nitrogen heterocyclic chemistry is in the synthesis of porphyrinoids octaethylisocorrole 102 and corphycene 103 have been synthesized by intramolecular cyclization of the corresponding tetrapyrrolic a,porphyrin derivatives have been obtained by tandem reactions (Section 6.2.3). 

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