Regiodivergent sulfonylarylation of 1,3-enynes via nickel/photoredox dual catalysis

• Published in: Chemical science (Cambridge) Vol. 12; no. 40; pp. 13564 - 13571
• Main Authors: Chen, Ya, Zhu, Kun, Huang, Qingqin, Lu, Yixin
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 20.10.2021; Royal Society of Chemistry; The Royal Society of Chemistry
• Subjects: Catalysis; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Dienes; Nickel; Photoredox catalysis; Physical Sciences; Science & Technology; Selectivity; Stereoselectivity; Sulfones; VISIBLE-LIGHT PHOTOREDOX
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/D1SC04320J

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.