Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines
Iron‐catalyzed ortho C−H arylation and methylation reactions of pivalophenone N−H imines are reported. The pivaloyl N−H imine proved an excellent directing group for the arylation with diarylzinc reagents in the presence of an iron‐diphosphine catalyst and 2,3‐dichlorobutane at room temperature. A s...
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sg-ntu-dr.10356-1439302023-02-28T19:48:19Z Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines Xu, Wengang Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Arylation C−H Activation Iron‐catalyzed ortho C−H arylation and methylation reactions of pivalophenone N−H imines are reported. The pivaloyl N−H imine proved an excellent directing group for the arylation with diarylzinc reagents in the presence of an iron‐diphosphine catalyst and 2,3‐dichlorobutane at room temperature. A similar catalytic system also allowed methylation with Me3Al at 70 °C. The pivaloyl imine of the product could be readily converted to a cyano group, thus allowing convenient preparation of ortho‐functionalized benzonitriles. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by the Ministry of Education (Singapore) and Nanyang Technological University (MOE2016-T2-2-043) 2020-10-02T01:01:01Z 2020-10-02T01:01:01Z 2019 Journal Article Xu, W., & Yoshikai, N. (2019). Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines. ChemSusChem, 12(13), 3049-3053. doi:10.1002/cssc.201900164 1864-5631 https://hdl.handle.net/10356/143930 10.1002/cssc.201900164 30786170 13 12 3049 3053 en ChemSusChem This is the accepted version of the following article: Xu, W., & Yoshikai, N. (2019). Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines. ChemSusChem, 12(13), 3049-3053. doi:10.1002/cssc.201900164, which has been published in final form at http://doi.org/10.1002/cssc.201900164. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf |
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Science::Chemistry Arylation C−H Activation Xu, Wengang Yoshikai, Naohiko Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| description |
Iron‐catalyzed ortho C−H arylation and methylation reactions of pivalophenone N−H imines are reported. The pivaloyl N−H imine proved an excellent directing group for the arylation with diarylzinc reagents in the presence of an iron‐diphosphine catalyst and 2,3‐dichlorobutane at room temperature. A similar catalytic system also allowed methylation with Me3Al at 70 °C. The pivaloyl imine of the product could be readily converted to a cyano group, thus allowing convenient preparation of ortho‐functionalized benzonitriles. |
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School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Xu, Wengang Yoshikai, Naohiko |
| format |
Article |
| author |
Xu, Wengang Yoshikai, Naohiko |
| author_sort |
Xu, Wengang |
| title |
Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| title_short |
Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| title_full |
Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| title_fullStr |
Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| title_full_unstemmed |
Iron-catalyzed ortho C−H arylation and methylation of pivalophenone N−H imines |
| title_sort |
iron-catalyzed ortho c−h arylation and methylation of pivalophenone n−h imines |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/143930 |
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