Chen Ya, Zhu Kun, Huang Qingqin, Lu Yixin
Department of Chemistry, National University of Singapore 3 Science Drive 3 Singapore 117543 Singapore
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City Fuzhou Fujian 350207 China.
Chem Sci. 2021 Sep 20;12(40):13564-13571. doi: 10.1039/d1sc04320j. eCollection 2021 Oct 20.
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 dual nickel and photoredox catalysis. Hinging on the nature of 1,3-enynes, diverse reaction pathways are feasible: synthesis of α-allenyl sulfones 1,4-sulfonylarylation, or preparation of ()-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.
1,3-烯炔的催化双官能化是一种高效且通用的方法，可快速组装多功能炔丙基化合物、丙二烯和1,3-二烯。由于1,3-烯炔的共轭结构产生多个反应中心，因此在这类加成反应中控制选择性一直是一项长期具有挑战性的任务。在此，我们提出了一种通过双镍和光氧化还原催化实现1,3-烯炔区域发散性磺酰芳基化的直接方法。基于1,3-烯炔的性质，多种反应途径是可行的：通过1,4-磺酰芳基化合成α-烯丙基砜，或通过3,4-磺酰芳基化以高化学、区域和立体选择性制备（）-1,3-二烯基砜。值得注意的是，这是首例将镍催化与光氧化还原催化相结合以实现1,3-烯炔高效通用双官能化的实例。
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