With advances in organoboron chemistry,boron-centered functional groups,especially alkyl boronic acids,which are widely available,bench stable,easy to prepare,minimally toxic,and structurally diverse,have become incre...With advances in organoboron chemistry,boron-centered functional groups,especially alkyl boronic acids,which are widely available,bench stable,easy to prepare,minimally toxic,and structurally diverse,have become increasingly attractive.However,their utility is limited by their high oxidation potentials.In this study,we overcame this limitation by complexing an inorganic base(K_(3)PO_(4))with alkyl boronic acids to decrease their oxidation potentials.Specifically,we present a powerful method for light-mediated deboronative cross-coupling reactions between alkyl boronic acids and aryl halides to afford products.This method demonstrated good functional group tolerance,and the mild conditions enabled the functionalization of drug molecules.In addition,the method could be extended to three-component carboacylation/carboarylation reactions of olefins to give products with high enantiomeric excess.Moreover,the reactions could be carried out under continuous-flow conditions,which enhanced the scalability,safety,and overall efficiency of the method.展开更多
Here,a new designed core/satellite gold nanoprobe was developed for detecting trace mount of benzoyl peroxide(BPO) based on its deboronation.This gold nanoassembly(the BE-Au NPs_(12/65)) wa s constructed via borate es...Here,a new designed core/satellite gold nanoprobe was developed for detecting trace mount of benzoyl peroxide(BPO) based on its deboronation.This gold nanoassembly(the BE-Au NPs_(12/65)) wa s constructed via borate ester formation between large 4-mercaptophenylboronic acid(MPBA) modified Au NPs(the MPBAAu NPs_(65),as cores) and small dopamine modified AuNPs(the D PA-AuNPs_(12),as satellites).Particularly,upon addition of BPO,it would trigger the deboronation for the BE-AuNPs_(12/65) probes accompanying with distinct color changes from blue,purple to wine red,which implied the disassembly of the core/satellite nanostructure after the breakage of carbon to boron chemical bond.By measuring the absorbance ratio at 665 nm and 545 nm,quantification of BPO was achieved in the range of 10.0-100.0 nmol/L,which could also be easily observed by naked eyes.The nanoprobe utilized a boronate deprotection mechanism and the LSPR properties of Au NPs to provide high selectivity for detecting BPO over similar ROS/RNS with the limit of detection as low as 7.2 nmol/L.The practical applicability of this assay was verified through successful determining BPO in flour samples,which demonstrated its great potentials in food safety field.展开更多
基金the National Natural Science Foundation of China(No.22271166)the Frontiers Science Center for New Organic Matter,Nankai University(No.63181206),for generous financial support。
文摘With advances in organoboron chemistry,boron-centered functional groups,especially alkyl boronic acids,which are widely available,bench stable,easy to prepare,minimally toxic,and structurally diverse,have become increasingly attractive.However,their utility is limited by their high oxidation potentials.In this study,we overcame this limitation by complexing an inorganic base(K_(3)PO_(4))with alkyl boronic acids to decrease their oxidation potentials.Specifically,we present a powerful method for light-mediated deboronative cross-coupling reactions between alkyl boronic acids and aryl halides to afford products.This method demonstrated good functional group tolerance,and the mild conditions enabled the functionalization of drug molecules.In addition,the method could be extended to three-component carboacylation/carboarylation reactions of olefins to give products with high enantiomeric excess.Moreover,the reactions could be carried out under continuous-flow conditions,which enhanced the scalability,safety,and overall efficiency of the method.
基金financial support from the National Natural Science Foundation of China(Nos.U1736201,21677019 and 41403021)Capital Health Research and Development of Special(No.2018-4-1014)the Key Research and Development Program of Beijing(No.D171100008317001)。
文摘Here,a new designed core/satellite gold nanoprobe was developed for detecting trace mount of benzoyl peroxide(BPO) based on its deboronation.This gold nanoassembly(the BE-Au NPs_(12/65)) wa s constructed via borate ester formation between large 4-mercaptophenylboronic acid(MPBA) modified Au NPs(the MPBAAu NPs_(65),as cores) and small dopamine modified AuNPs(the D PA-AuNPs_(12),as satellites).Particularly,upon addition of BPO,it would trigger the deboronation for the BE-AuNPs_(12/65) probes accompanying with distinct color changes from blue,purple to wine red,which implied the disassembly of the core/satellite nanostructure after the breakage of carbon to boron chemical bond.By measuring the absorbance ratio at 665 nm and 545 nm,quantification of BPO was achieved in the range of 10.0-100.0 nmol/L,which could also be easily observed by naked eyes.The nanoprobe utilized a boronate deprotection mechanism and the LSPR properties of Au NPs to provide high selectivity for detecting BPO over similar ROS/RNS with the limit of detection as low as 7.2 nmol/L.The practical applicability of this assay was verified through successful determining BPO in flour samples,which demonstrated its great potentials in food safety field.
