Copper‐Catalyzed [2+2+2] Modular Synthesis of Multisubstituted Pyridines: Alkenylation of Nitriles with Vinyliodonium Salts. Issue 17 (28th March 2017)

• Record Type: Journal Article
• Authors: Sheng, Jinyu; Wang, Yong; Su, Xiang; He, Ru; Chen, Chao
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 17(2017)
• Page Start: 4824
• Page End: 4828
• Publication Date: 2017-03-28
• Subjects: alkynes -- copper -- heterocycles -- multicomponent reactions -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201700696
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A [2+2+2] modular synthesis of multisubstituted pyridines, with excellent regioselectivity, has been realized by copper catalysisand involves three distinct components: vinyliodonium salts, nitriles, and alkynes. The reactions proceeded with the facile formation of an aza‐butadienylium intermediate by alkenylation of the nitrile with a vinyliodonium salt. Moreover, the alkynes in the reaction were extended to alkenes, which are an advantage of expense and relative scarceness of alkynes. Abstract : Three to one ! A [2+2+2] modular synthesis of multisubstituted pyridines with excellent regioselectivity has been realized by copper catalysis and involves three distinct components: vinyliodonium salts, nitriles, and alkynes. The reactions proceeded with the facile formation of an aza‐butadienylium intermediate by alkenylation of the nitrile with a vinyliodonium salt.