Insertion reactions isoquinoline synthesis

Alkynes have also been used with cesium acetate both for alkynylation and in the synthesis of p)ridines and isoquinolines.The alkynylation of aromatics was promoted by the use of 8-aminoquinoline as a directing group. However, cesium acetate was used in stoichiometric amount in addition to palladium acetate (eq 5). Other insertion reactions have been performed where cesium acetate was used as an additive for nonnatural amino acid synthesis via the addition of a phenyl group during the synthetic route. Also, iodination with palladium acetate and am-ination with a rhodium complex have been successful with cesium acetate as a base. 

Recently, Glorias discovered a Rh(III)-catalyzed coupling of oximes with electron-deficient diazo compounds to give iV-oxides of isoquinoline and pyridine [55]. The reaction proceeds with the liberation of H2O and Nj as by-products. In this reaction, the insertion of Rh-carbene into ortho-C-H bond followed by intramolecular dehydrative annulation plausibly accounts for the generation of Af-oxides (Eqs. (5.107) and (5.108)). The diazo compounds functioned as equivalents of electron-deficient alkynes, enriching the product diversity of isoquinoline and pyridine synthesis. 

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