1994
DOI: 10.3987/com-94-s(b)38
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Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

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Cited by 20 publications
(15 citation statements)
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“…Only the reactions of 4‐chlorocarbostyrils of type 8 with 3‐alkyl‐ or 3‐alkoxy‐substituents in the 3‐position did not proceed. In ref 12. the intermediate sulfinates were not isolated.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Only the reactions of 4‐chlorocarbostyrils of type 8 with 3‐alkyl‐ or 3‐alkoxy‐substituents in the 3‐position did not proceed. In ref 12. the intermediate sulfinates were not isolated.…”
Section: Resultsmentioning
confidence: 99%
“…Another method, however, which was described recently,12 allowed us to introduce the nitrile group at the 4‐position of chlorocarbostyrils 8 under rather mild conditions of 120 °C by using sodium or lithium p ‐toluenesulfinate as intermediates in dimethylformamide as the solvent. Only the reactions of 4‐chlorocarbostyrils of type 8 with 3‐alkyl‐ or 3‐alkoxy‐substituents in the 3‐position did not proceed.…”
Section: Resultsmentioning
confidence: 99%
“…Several nucleophiles can displace the halogen atom. For example, reactions on 1-chloro or 1-bromo-substituted isoquinolines with water [368], sodium hydroxide [368], alkoxides [369][370][371], thioalkoxides [372], trimethylsilanolate [373], ammonia [374], amides [375], amines [376], potassium cyanide [377], and phosphorus ylides [378] have been reported.…”
Section: Reactions With Oxidizing Reagentsmentioning
confidence: 99%
“…This feature and the intrinsic nucleophilicity of sulfinates afford an ideal combination for applications of these anions as Lewis bases in organocatalysis. However, to the best of our knowledge, very few examples of sulfinate‐organocatalyzed reactions have been reported so far in the literature . The main approach in the area refers to the so‐called Padwa reaction, which was introduced in the late 80's .…”
Section: Introductionmentioning
confidence: 99%