Preparation of 4-heteroaryl-4-cyanopiperidines via SNAr substitution reactions

The scope and limitations of SNAr substitution reactions of metalated 4-cyanopiperidines with heterocyclic halides were explored. These facile reactions provide rapid access to a wide range of 4-heteroaryl-4-cyanopiperidines and have resulted in improved yields, faster reaction times, and lower temp...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 46; pp. 6303 - 6306
Main Authors Chang, Ronald K., Di Marco, Christina N., Pitts, Daniel R., Greshock, Thomas J., Kuduk, Scott D.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 18.11.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA-ARYLATION
NITRILES
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Summary:The scope and limitations of SNAr substitution reactions of metalated 4-cyanopiperidines with heterocyclic halides were explored. These facile reactions provide rapid access to a wide range of 4-heteroaryl-4-cyanopiperidines and have resulted in improved yields, faster reaction times, and lower temperatures than previously published synthetic methods. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2009.08.123