Visible-light-induced, autopromoted nickel-catalyzed three-component arylsulfonation of 1,3-enynes and mechanistic in-sights

被引:24
作者
Hu, Duo-Duo [1 ]
Gao, Qian [1 ]
Dai, Jing-Cheng [1 ]
Cui, Ru [1 ]
Li, Yuan-Bo [1 ]
Li, Yuan-Ming [2 ,3 ]
Zhou, Xiao-Guo [2 ,3 ]
Bian, Kang-Jie [1 ]
Wu, Bing-Bing [1 ]
Zhang, Kai-Fan [1 ]
Wang, Xi-Sheng [1 ]
Li, Yan [1 ]
机构
[1] Univ Sci & Technol China, Ctr Excellence Mol Synth CAS, Dept Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[3] Univ Sci & Technol China, Dept Chem Phys, Hefei 230026, Peoples R China
基金
美国国家科学基金会;
关键词
light-induced; autopromoted; ligand to metal charge transfer; nickel; allene; TRANSITION-METAL; PHOTOREDOX; COMPLEX; ALLENES;
D O I
10.1007/s11426-021-1193-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A light-induced, nickel-catalyzed three-component arylsulfonation of 1,3-enynes in the absence of photocatalyst is reported. This methodology exhibited mild conditions, broad scope and high efficiency, and its synthetic utility has been demonstrated by a concise total synthesis of sulfone-containing drug molecule. Detailed mechanistic studies indicated that this light induced nickel catalysis is autopromoted by in situ produced allene, which plays a key role as co-ligand in the photoactive excited state Ni(I) species for the LMCT process. The detailed elucidation of this light-induced nickel catalytic cycle may shed some lights on the exploitation of new catalytic activity and establishment of novel methods.
引用
收藏
页码:753 / 761
页数:9
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