Regiodivergent sulfonylarylation of 1, 3-enynes via nickel/photoredox dual catalysis. Issue 40 (29th September 2021)

• Record Type: Journal Article
• Authors: Chen, Ya; Zhu, Kun; Huang, Qingqin; Lu, Yixin
• Is Part Of: Chemical science. Volume 12:Issue 40(2021)
• Page Start: 13564
• Page End: 13571
• Publication Date: 2021-09-29
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc04320j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A mild reaction protocol for regiodivergent sulfonylarylation of 1, 3-enynes via dual nickel and photoredox catalysis has been developed, which led to efficient synthesis of α-allenyl sulfones or 1, 3-dienyl sulfones. Abstract : Catalytic difunctionalization of 1, 3-enynes represents an efficient and versatile approach to rapidly assemble multifunctional propargylic compounds, allenes and 1, 3-dienes. Controlling selectivity in such addition reactions has been a long-standing challenging task due to multiple reactive centers resulting from the conjugated structure of 1, 3-enynes. Herein, we present a straightforward method for regiodivergent sulfonylarylation of 1, 3-enynes via dual nickel and photoredox catalysis. Hinging on the nature of 1, 3-enynes, diverse reaction pathways are feasible: synthesis of α-allenyl sulfones via 1, 4-sulfonylarylation, or preparation of ( E )-1, 3-dienyl sulfones with high chemo-, regio- and stereoselectivity through 3, 4-sulfonylarylation. Notably, this is the first example that nickel and photoredox catalysis are merged to achieve efficient and versatile difunctionalization of 1, 3-enynes.