A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditi...A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditions,as well as great functional group tolerance.Micelles with negatively charged polar surface and hydrophobic core formed from sodium dodecyl sulfate serve as an ideal medium for visible-light mediated radical reaction of cationic pyridine salt and imidazo[1,2-a]pyridine in aqueous phase.The electrostatic interaction between positively charged N-aminopyridinium and negatively charged surface of micelles is of great significance in this method.展开更多
Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry.Herein,we report a multi-component,regiose...Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry.Herein,we report a multi-component,regioselective bis-acylation of olefins by merging NHC organocatalysis and photoredox catalysis.With this protocol,a broad range of 1,4-diketones could be rapidly assembled using bench-stable feedstock materials.The robustness of this method was further evaluated by sensitivity screening,and good reproductivity was observed.Moreover,the diketone products could be readily converted into functionalized heterocycles,such as multi-substituted furan,pyrrole,and pyridazine.Mechanistic investigations shed light on the NHC and photoredox dual catalytic radical reaction mechanism.展开更多
The palladium-catalysed[3+2]annulation of vinylethylene carbonates(VECs)and ketones remains challenging in organic synthesis.Herein,we successfully achieved the[3+2]annulation of tryptanthrin-based ketones and VECs fo...The palladium-catalysed[3+2]annulation of vinylethylene carbonates(VECs)and ketones remains challenging in organic synthesis.Herein,we successfully achieved the[3+2]annulation of tryptanthrin-based ketones and VECs for the efficient synthesis of indoloquinazolinone derivatives with generally excellent yields and good diastereoselectivity.Notably,the asymmetric version of this[3+2]annulation can also be achieved by using a chiral spiroketal-based diphosphine ligand.In addition,preliminary biological studies reveal that some of the products exhibit promising antibacterial activity.展开更多
基金We thank the National Natural Science Foundation of China(Grant Nos.21901216 and 21871031)the Fund of Science and Technology Agency of Chengdu(2019-YF09-00049-SN)+1 种基金the Open Project Program of Irradiation Preservation Technology Key Laboratory of Sichuan Province,Sichuan Institute of Atomic Energy(No.FZBC2020002)the Sichuan Science and Technology Program(2020YFH0061,2020YJ0222,2021JDRC0018,2021YFS0092,2021YFSY0041,2021YFH0064).
文摘A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditions,as well as great functional group tolerance.Micelles with negatively charged polar surface and hydrophobic core formed from sodium dodecyl sulfate serve as an ideal medium for visible-light mediated radical reaction of cationic pyridine salt and imidazo[1,2-a]pyridine in aqueous phase.The electrostatic interaction between positively charged N-aminopyridinium and negatively charged surface of micelles is of great significance in this method.
基金the National Natural Science Foundation of China(NSFC,Nos.22071011,21871031,22271028 and 82073998)Longquan Talents Program,the Science&Technology Department of Sichuan Province(Nos.2021YJ0404,2022JDRC0045 and 2023NSFSC1081)the innovative project of Chengdu University is gratefully acknowledged.
文摘Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry.Herein,we report a multi-component,regioselective bis-acylation of olefins by merging NHC organocatalysis and photoredox catalysis.With this protocol,a broad range of 1,4-diketones could be rapidly assembled using bench-stable feedstock materials.The robustness of this method was further evaluated by sensitivity screening,and good reproductivity was observed.Moreover,the diketone products could be readily converted into functionalized heterocycles,such as multi-substituted furan,pyrrole,and pyridazine.Mechanistic investigations shed light on the NHC and photoredox dual catalytic radical reaction mechanism.
基金support from the NSFC(21871031 and 22071011)the Science&Technology Department of Sichuan Province(2021YJ0404)the Longquan Talents Program,and the start-up funding from Chengdu University is gratefully acknowledged.
文摘The palladium-catalysed[3+2]annulation of vinylethylene carbonates(VECs)and ketones remains challenging in organic synthesis.Herein,we successfully achieved the[3+2]annulation of tryptanthrin-based ketones and VECs for the efficient synthesis of indoloquinazolinone derivatives with generally excellent yields and good diastereoselectivity.Notably,the asymmetric version of this[3+2]annulation can also be achieved by using a chiral spiroketal-based diphosphine ligand.In addition,preliminary biological studies reveal that some of the products exhibit promising antibacterial activity.
