Ethan Zars, Lisa Pick, Achala Kankanamge, Michael R Gau, Karsten Meyer, Daniel J Mindiola
{"title":"C<sub>sp<sup>2</sup></sub>-H/F bond activation and borylation with iron.","authors":"Ethan Zars, Lisa Pick, Achala Kankanamge, Michael R Gau, Karsten Meyer, Daniel J Mindiola","doi":"10.1039/d4cc04127e","DOIUrl":null,"url":null,"abstract":"<p><p>Reduction of [K<sub>2</sub>{(<sup><i>t</i>Bu</sup>pyrr<sub>2</sub>pyr)Fe}<sub>2</sub>(μ-N<sub>2</sub>)] (1) with two equiv. of KC<sub>8</sub> in the presence of crown-ether 18-C-6 yields the N<sub>2</sub> adduct [{K(18-C-6)}<sub>2</sub>(<sup><i>t</i>Bu</sup>pyrr<sub>2</sub>pyr)Fe(N<sub>2</sub>)] (2). Complex 2 heterolytically splits the C<sub>sp<sup>2</sup></sub>-H bond of benzene to form [{K(18-C-6)}(<sup><i>t</i>Bu</sup>pyrr<sub>2</sub>pyr)Fe(C<sub>6</sub>H<sub>5</sub>)] (3), whereby usage of a diboron B<sub>2</sub>pin<sub>2</sub> promotes hydride elimination to form the salt [K(18-C-6)HB<sub>2</sub>Pin<sub>2</sub>] (4). Similarly, 3 can also be formed by cleavage of the C-F bond of fluorobenzene. Reaction of 3 with ClBcat yields [K(18-C-6)(thf)<sub>2</sub>][(<sup><i>t</i>Bu</sup>pyrr<sub>2</sub>pyr)FeCl] (5) and PhBcat and the former can be reduced to 2 to complete a synthetic cycle for heterolytic benzene C-H activation and borylation.</p>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":null,"pages":null},"PeriodicalIF":4.3000,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4cc04127e","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Reduction of [K2{(tBupyrr2pyr)Fe}2(μ-N2)] (1) with two equiv. of KC8 in the presence of crown-ether 18-C-6 yields the N2 adduct [{K(18-C-6)}2(tBupyrr2pyr)Fe(N2)] (2). Complex 2 heterolytically splits the Csp2-H bond of benzene to form [{K(18-C-6)}(tBupyrr2pyr)Fe(C6H5)] (3), whereby usage of a diboron B2pin2 promotes hydride elimination to form the salt [K(18-C-6)HB2Pin2] (4). Similarly, 3 can also be formed by cleavage of the C-F bond of fluorobenzene. Reaction of 3 with ClBcat yields [K(18-C-6)(thf)2][(tBupyrr2pyr)FeCl] (5) and PhBcat and the former can be reduced to 2 to complete a synthetic cycle for heterolytic benzene C-H activation and borylation.
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