Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenin...Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenindole derivatives.The advantages of this strategy include mild and transition-metal-free conditions,broad functional group tolerance,the use of simple and easily accessible seleniium powder and alkyl halides as coupling partners.More importantly,the reaction proceeded smoothly with a large scale(>10 g,>90%yield),which further highlighted the potential application of this selenation strategy.展开更多
Planar chiral ferrocenes are widely applied in organic synthesis,materials science,and medicinal chemistry,but their synthesis is not trivial.Herein,a highly efficient synthesis of planar chiral ferrocene-based pyridi...Planar chiral ferrocenes are widely applied in organic synthesis,materials science,and medicinal chemistry,but their synthesis is not trivial.Herein,a highly efficient synthesis of planar chiral ferrocene-based pyridine derivatives via Rh(I)-catalyzed direct coupling of pyridylferrocenes with aryl halides was developed.Good yields and excellent enantioselectivity(95–>99%ee)are obtained for a wide range of substrates.The compatibility of gram-scale synthesis and relatively low catalyst loading(down to 1 mol%based on[Rh])enhance the practicality of the current method.The generated coupling products can be readily transformed into chiral ligands.Mechanistic studies suggest that the C–H bond cleavage of pyridylferrocene may be a reversible step and not the rate-determining step.Significant nonlinear effects indicate the existence of multiple metals or ligands in the active catalyst.展开更多
基金the National Natural Science Foundation of China(No.21672157)PAPD,the project of scientific and technologic infrastructure of Suzhou(No.SZS201708)+1 种基金Natural Science Foundation of Jiangsu Province(No.BK20200874)Natural Science Foundation for colleges and universities in Jiangsu Province(No.20KJD150001)。
文摘Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenindole derivatives.The advantages of this strategy include mild and transition-metal-free conditions,broad functional group tolerance,the use of simple and easily accessible seleniium powder and alkyl halides as coupling partners.More importantly,the reaction proceeded smoothly with a large scale(>10 g,>90%yield),which further highlighted the potential application of this selenation strategy.
基金the National Key R&D Program of China(2016YFA0202900),NSFC(21821002,91856201)the CAS(XDB20000000,QYZDY-SSW-SLH012)Science and Technology Commission of Shanghai Municipality(18JC1411302)。
文摘Planar chiral ferrocenes are widely applied in organic synthesis,materials science,and medicinal chemistry,but their synthesis is not trivial.Herein,a highly efficient synthesis of planar chiral ferrocene-based pyridine derivatives via Rh(I)-catalyzed direct coupling of pyridylferrocenes with aryl halides was developed.Good yields and excellent enantioselectivity(95–>99%ee)are obtained for a wide range of substrates.The compatibility of gram-scale synthesis and relatively low catalyst loading(down to 1 mol%based on[Rh])enhance the practicality of the current method.The generated coupling products can be readily transformed into chiral ligands.Mechanistic studies suggest that the C–H bond cleavage of pyridylferrocene may be a reversible step and not the rate-determining step.Significant nonlinear effects indicate the existence of multiple metals or ligands in the active catalyst.
