Journal
CHEMICAL SCIENCE
Volume 12, Issue 40, Pages 13564-13571Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc04320j
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Funding
- Singapore National Research Foundation, Prime Minister's Office [R-143-000-A15-281]
- National University of Singapore [C-141-000-092-001]
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The study presents a method for regiodivergent sulfonylarylation of 1,3-enynes via dual nickel and photoredox catalysis, offering diverse reaction pathways and the first example of merging nickel and photoredox catalysis for efficient and versatile difunctionalization of 1,3-enynes.
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 alpha-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.
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