Chinese Journal of Organic Chemistry >
Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes
Received date: 2021-06-07
Revised date: 2021-07-14
Online published: 2021-07-20
Supported by
National Natural Science Foundation of China(21971090); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions and National College Studentʼs Innovation and Entrepreneurship Training Program(202010320060Z)
A new visible-light-driven photocatalytic Kharasch-type addition of 1,6-enynes was reported. By using the characteristics of the in-situ-generation of trihalomethyl radicals from photocatalytic reduction of trichloromethane bromide and carbon tetrabromide, fac-Ir(ppy)3-catalyzed Kharasch-type addition of 1,6-enynes of these polyhalogenated hydrocarbon substrates at room temperature was conducted under visible-light irradiation, regioselectively affording 1-indanone derivatives with an exocyclic double bond and a quaternary carbon in moderate to good yields. Based on the experimental results and literature reports, a reasonable reaction mechanism was proposed, which involved the in-situ-generation of trihalomethyl radicals, radical-induced addition-cyclization and radical cross coupling. In addition, this protocol featured wide substrate scope, high functional group compatibility, 100% atomic utilization, and mild conditions as well as simple operation. It provides a green, mild, and efficient synthetic strategy for the construction of 1-indanone skeleton with potential application, which is consistent with the concept of green chemistry.
Key words： Kharasch-type addition; photocatalysis; 1,6-enynes; 1-indanones
Fangzhou Geng , Shichao Wang , Kexian Song , Wenjuan Hao , Bo Jiang . Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4815 -4824 . DOI: 10.6023/cjoc202106014
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