Regio-divergent nickel catalysis: intramolecular [4+2] and [2+2] cycloaddition reactions between vinylallenes and alkynes. Issue 85 (12th October 2021)

• Record Type: Journal Article
• Authors: Arai, Shigeru; Inagaki, Saki; Nakajima, Masaya; Nishida, Atsushi
• Is Part Of: Chemical communications. Volume 57:Issue 85(2021)
• Page Start: 11268
• Page End: 11271
• Publication Date: 2021-10-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc03942c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Vinylallenes have been recognized as versatile C2 and C4 components for nickel-catalyzed intramolecular [4+2] and [2+2] cycloadditions. Abstract : Vinylallenes have been recognized as versatile C2 and C4 components for nickel-catalyzed intramolecular [4+2] and [2+2] cycloadditions. The former reaction was promoted by a Ni(0) complex (up to quantitative yield), and a Ni(ii ) salt was a key species for the latter reaction to give the corresponding regio- and stereocontrolled cycloadducts (up to 88% yield). DFT studies revealed that both reaction pathways involve a concerted mechanism through the activation of different C–C multiple bonds in the substrates.