Organic Photocatalytic Cyclization of Polyenes: A Visible-Light-Mediated Radical Cascade Approach
Zhongbo Yang
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Search for more papers by this authorHan Li
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Search for more papers by this authorDr. Long Zhang
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Search for more papers by this authorCorresponding Author
Prof. Ming-Tian Zhang
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Ming-Tian Zhang, Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Sanzhong Luo, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn
Search for more papers by this authorProf. Dr. Jin-Pei Cheng
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Sanzhong Luo
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Ming-Tian Zhang, Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Sanzhong Luo, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn
Search for more papers by this authorZhongbo Yang
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Search for more papers by this authorHan Li
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Search for more papers by this authorDr. Long Zhang
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Search for more papers by this authorCorresponding Author
Prof. Ming-Tian Zhang
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Ming-Tian Zhang, Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Sanzhong Luo, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn
Search for more papers by this authorProf. Dr. Jin-Pei Cheng
Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Sanzhong Luo
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449 http://luosz.iccas.ac.cn
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China)
Ming-Tian Zhang, Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China)
Sanzhong Luo, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn
Search for more papers by this authorGraphical Abstract
A visible improvement: A visible-light-mediated, organic photocatalytic radical cascade cyclization of polyprenoids has been developed. By combination of eosin Y as photocatalyst and hexafluoro-2-propanol as solvent, the desired cascade cyclization products are obtained in good yields and high stereoselectivities (see scheme; HFIP=hexafluoro-2-propanol).
Abstract
A visible-light-mediated, organic photocatalytic stereoselective radical cascade cyclization of polyprenoids is described. The desired cascade cyclization products are achieved in good yields and high stereoselectivities with eosin Y as photocatalyst in hexafluoro-2-propanol. The catalyst system is also suitable for 1,3-dicarbonyl compounds, which require only catalytic amounts of LiBr to promote the formation of the corresponding enols.
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