Full metadata record
DC Field | Value | Language |
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dc.contributor.author | 남원우 | * |
dc.contributor.author | 이용민 | * |
dc.date.accessioned | 2023-04-14T16:31:11Z | - |
dc.date.available | 2023-04-14T16:31:11Z | - |
dc.date.issued | 2023 | * |
dc.identifier.issn | 0002-7863 | * |
dc.identifier.other | OAK-33138 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/264871 | - |
dc.description.abstract | The development of catalytic systems capable of oxygenating unactivated C-H bonds with excellent site-selectivity and functional group tolerance under mild conditions remains a challenge. Inspired by the secondary coordination sphere (SCS) hydrogen bonding in metallooxygenases, reported herein is an SCS solvent hydrogen bonding strategy that employs 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a strong hydrogen bond donor solvent to enable remote C-H hydroxylation in the presence of basic aza-heteroaromatic rings with a low loading of a readily available and inexpensive manganese complex as a catalyst and hydrogen peroxide as a terminal oxidant. We demonstrate that this strategy represents a promising compliment to the current state-of-the-art protection approaches that rely on precomplexation with strong Lewis and/or Brønsted acids. Mechanistic studies with experimental and theoretical approaches reveal the existence of a strong hydrogen bonding between the nitrogen-containing substrate and HFIP, which prevents the catalyst deactivation by nitrogen binding and deactivates the basic nitrogen atom toward oxygen atom transfer and the α-C-H bonds adjacent to the nitrogen center toward H-atom abstraction. Moreover, the hydrogen bonding exerted by HFIP has also been demonstrated not only to facilitate the O-O bond heterolytic cleavage of a putative MnIII-OOH precursor to generate MnV(O)(OC(O)CH2Br) as an active oxidant but also to affect the stability and the activity of MnV(O)(OC(O)CH2Br). © 2023 American Chemical Society. | * |
dc.language | English | * |
dc.publisher | American Chemical Society | * |
dc.title | Hydrogen Bonding-Assisted and Nonheme Manganese-Catalyzed Remote Hydroxylation of C-H Bonds in Nitrogen-Containing Molecules | * |
dc.type | Article | * |
dc.relation.issue | 9 | * |
dc.relation.volume | 145 | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 5456 | * |
dc.relation.lastpage | 5466 | * |
dc.relation.journaltitle | Journal of the American Chemical Society | * |
dc.identifier.doi | 10.1021/jacs.2c13832 | * |
dc.identifier.wosid | WOS:000935781400001 | * |
dc.identifier.scopusid | 2-s2.0-85148770927 | * |
dc.author.google | Chen J. | * |
dc.author.google | Song W. | * |
dc.author.google | Yao J. | * |
dc.author.google | Wu Z. | * |
dc.author.google | Lee Y.-M. | * |
dc.author.google | Wang Y. | * |
dc.author.google | Nam W. | * |
dc.author.google | Wang B. | * |
dc.contributor.scopusid | 남원우(7006569723) | * |
dc.contributor.scopusid | 이용민(36546331100;35233855500;57192113229) | * |
dc.date.modifydate | 20240426135715 | * |