The design and synthesis of a novel organic photocatalyst(OPC)have attracted broad interest from both the organic chemistry and polymer community.Herein,we presented a visible-light-induced alkylarylation of alkenes s...The design and synthesis of a novel organic photocatalyst(OPC)have attracted broad interest from both the organic chemistry and polymer community.Herein,we presented a visible-light-induced alkylarylation of alkenes strategy for core modification of 5,10-diaryl-5,10-dihydrophenazines(DADHPs)under metal-and additive-free conditions,with the aim to develop powerful photocatalyst for organocatalyzed atom transfer radical polymerization(O-ATRP).Good tolerance for a wide variety of functional groups and affording the corresponding tetrasubstituted products in moderate to good yields were achieved in the batch and flow reactor.The experimental and computational mechanistic study confirmed that DADHPs’radical cations andπ-πstacking interactions played important roles in the alkylarylation of alkenes.A series of the tetrasubstituted DADHPs were directly synthesized from the corresponding noncore-modified phenazines,which were demonstrated to be effective organic photoredox catalysts for O-ATRP.Light responsive nature,controlled polymerization manner,and welldefined poly(methyl methacrylate)were achieved via tetrasubstituted DADHPs mediated O-ATRP.展开更多
基金The research was supported by the National Natural Science Foundation of China(No.22278221)the National Key Research and Development Program of China(No.2021YFC2101900)the Natural Science Foundation of Jiangsu Province(No.BK20212003).We also appreciated the high-performance center of Nanjing Tech University for supporting the computational resources.
文摘The design and synthesis of a novel organic photocatalyst(OPC)have attracted broad interest from both the organic chemistry and polymer community.Herein,we presented a visible-light-induced alkylarylation of alkenes strategy for core modification of 5,10-diaryl-5,10-dihydrophenazines(DADHPs)under metal-and additive-free conditions,with the aim to develop powerful photocatalyst for organocatalyzed atom transfer radical polymerization(O-ATRP).Good tolerance for a wide variety of functional groups and affording the corresponding tetrasubstituted products in moderate to good yields were achieved in the batch and flow reactor.The experimental and computational mechanistic study confirmed that DADHPs’radical cations andπ-πstacking interactions played important roles in the alkylarylation of alkenes.A series of the tetrasubstituted DADHPs were directly synthesized from the corresponding noncore-modified phenazines,which were demonstrated to be effective organic photoredox catalysts for O-ATRP.Light responsive nature,controlled polymerization manner,and welldefined poly(methyl methacrylate)were achieved via tetrasubstituted DADHPs mediated O-ATRP.
