FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W4318474559> ?p ?o ?g. }

• W4318474559 endingPage "2294" @default.
• W4318474559 startingPage "2286" @default.
• W4318474559 abstract "[(NacNac)Zn(DMT)][B(C6F5)4], 1, (NacNac = {(2,6- i Pr2H3C6)N(CH3)C}2CH), DMT = N,N-dimethyl-4-toluidine), was synthesized via two routes starting from either (NacNac)ZnEt or (NacNac)ZnH. Complex 1 is an effective (pre)catalyst for the C-H borylation of (hetero)arenes using catecholborane (CatBH) with H2 the only byproduct. The scope included weakly activated substrates such as 2-bromothiophene and benzothiophene. Computational studies elucidated a plausible reaction mechanism that has an overall free energy span of 22.4 kcal/mol (for N-methylindole borylation), consistent with experimental observations. The calculated mechanism starting from 1 proceeds via the displacement of DMT by CatBH to form [(NacNac)Zn(CatBH)]+, D, in which CatBH binds via an oxygen to zinc which makes the boron center much more electrophilic based on the energy of the CatB-based LUMO. Combinations of D and DMT act as a frustrated Lewis pair (FLP) to effect C-H borylation in a stepwise process via an arenium cation that is deprotonated by DMT. Subsequent B-H/[H-DMT]+ dehydrocoupling and displacement from the coordination sphere of zinc of CatBAr by CatBH closes the cycle. The calculations also revealed a possible catalyst decomposition pathway involving hydride transfer from boron to zinc to form (NacNac)ZnH which reacts with CatBH to ultimately form Zn(0). In addition, the key rate-limiting transition states all involve the base, thus fine-tuning of the steric and electronic parameters of the base enabled a further minor enhancement in the C-H borylation activity of the system. Outlining the mechanism for all steps of this FLP-mediated process will facilitate the development of other main group FLP catalysts for C-H borylation and other transformations." @default.
• W4318474559 created "2023-01-30" @default.
• W4318474559 creator A5003220010 @default.
• W4318474559 creator A5011183860 @default.
• W4318474559 creator A5023948794 @default.
• W4318474559 creator A5043306923 @default.
• W4318474559 creator A5068147047 @default.
• W4318474559 creator A5077488162 @default.
• W4318474559 date "2023-01-30" @default.
• W4318474559 modified "2023-09-26" @default.
• W4318474559 title "Understanding and Expanding Zinc Cation/Amine Frustrated Lewis Pair Catalyzed C–H Borylation" @default.
• W4318474559 cites W1260922102 @default.
• W4318474559 cites W1524847915 @default.
• W4318474559 cites W1984737964 @default.
• W4318474559 cites W1985495475 @default.
• W4318474559 cites W1997786398 @default.
• W4318474559 cites W2055673693 @default.
• W4318474559 cites W2101603110 @default.
• W4318474559 cites W2136689522 @default.
• W4318474559 cites W2137380454 @default.
• W4318474559 cites W2141705345 @default.
• W4318474559 cites W2305202522 @default.
• W4318474559 cites W2594353993 @default.
• W4318474559 cites W2754013900 @default.
• W4318474559 cites W2902770012 @default.
• W4318474559 cites W2945966347 @default.
• W4318474559 cites W3012643120 @default.
• W4318474559 cites W3016314100 @default.
• W4318474559 cites W3032125938 @default.
• W4318474559 cites W3043542545 @default.
• W4318474559 cites W3108546850 @default.
• W4318474559 cites W3125075588 @default.
• W4318474559 cites W3161192462 @default.
• W4318474559 cites W3172354340 @default.
• W4318474559 cites W3202270132 @default.
• W4318474559 cites W3204733712 @default.
• W4318474559 cites W4220838352 @default.
• W4318474559 cites W4224242201 @default.
• W4318474559 cites W4282913272 @default.
• W4318474559 cites W4283218066 @default.
• W4318474559 cites W4292438726 @default.
• W4318474559 cites W4293149865 @default.
• W4318474559 cites W4311662579 @default.
• W4318474559 doi "https://doi.org/10.1021/acscatal.2c05995" @default.
• W4318474559 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/36846822" @default.
• W4318474559 hasPublicationYear "2023" @default.
• W4318474559 type Work @default.
• W4318474559 citedByCount "3" @default.
• W4318474559 countsByYear W43184745592023 @default.
• W4318474559 crossrefType "journal-article" @default.
• W4318474559 hasAuthorship W4318474559A5003220010 @default.
• W4318474559 hasAuthorship W4318474559A5011183860 @default.
• W4318474559 hasAuthorship W4318474559A5023948794 @default.
• W4318474559 hasAuthorship W4318474559A5043306923 @default.
• W4318474559 hasAuthorship W4318474559A5068147047 @default.
• W4318474559 hasAuthorship W4318474559A5077488162 @default.
• W4318474559 hasBestOaLocation W43184745591 @default.
• W4318474559 hasConcept C118629725 @default.
• W4318474559 hasConcept C122085161 @default.
• W4318474559 hasConcept C145148216 @default.
• W4318474559 hasConcept C155647269 @default.
• W4318474559 hasConcept C161790260 @default.
• W4318474559 hasConcept C163638829 @default.
• W4318474559 hasConcept C178790620 @default.
• W4318474559 hasConcept C185592680 @default.
• W4318474559 hasConcept C188328357 @default.
• W4318474559 hasConcept C201194858 @default.
• W4318474559 hasConcept C2776413204 @default.
• W4318474559 hasConcept C2777961443 @default.
• W4318474559 hasConcept C2780263894 @default.
• W4318474559 hasConcept C2781076698 @default.
• W4318474559 hasConcept C39679061 @default.
• W4318474559 hasConcept C50027330 @default.
• W4318474559 hasConcept C512968161 @default.
• W4318474559 hasConcept C544153396 @default.
• W4318474559 hasConcept C63338738 @default.
• W4318474559 hasConcept C71240020 @default.
• W4318474559 hasConcept C75473681 @default.
• W4318474559 hasConceptScore W4318474559C118629725 @default.
• W4318474559 hasConceptScore W4318474559C122085161 @default.
• W4318474559 hasConceptScore W4318474559C145148216 @default.
• W4318474559 hasConceptScore W4318474559C155647269 @default.
• W4318474559 hasConceptScore W4318474559C161790260 @default.
• W4318474559 hasConceptScore W4318474559C163638829 @default.
• W4318474559 hasConceptScore W4318474559C178790620 @default.
• W4318474559 hasConceptScore W4318474559C185592680 @default.
• W4318474559 hasConceptScore W4318474559C188328357 @default.
• W4318474559 hasConceptScore W4318474559C201194858 @default.
• W4318474559 hasConceptScore W4318474559C2776413204 @default.
• W4318474559 hasConceptScore W4318474559C2777961443 @default.
• W4318474559 hasConceptScore W4318474559C2780263894 @default.
• W4318474559 hasConceptScore W4318474559C2781076698 @default.
• W4318474559 hasConceptScore W4318474559C39679061 @default.
• W4318474559 hasConceptScore W4318474559C50027330 @default.
• W4318474559 hasConceptScore W4318474559C512968161 @default.
• W4318474559 hasConceptScore W4318474559C544153396 @default.
• W4318474559 hasConceptScore W4318474559C63338738 @default.
• W4318474559 hasConceptScore W4318474559C71240020 @default.

• next