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- W2938874913 endingPage "8023" @default.
- W2938874913 startingPage "8018" @default.
- W2938874913 abstract "Abstract Herein, we report the meta ‐nitration of arenes bearing ortho / para directing group(s) using the iridium‐catalyzed C−H borylation reaction followed by a newly developed copper(II)‐catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one‐pot fashion. This protocol allows the synthesis of meta ‐nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho / para ‐directing groups, such as −F, −Cl, −Br, −CH 3 , −Et, − i Pr −OCH 3 , and −OCF 3 . It also provides regioselective access to the nitro derivatives of π‐electron‐deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late‐stage modification of complex molecules and also in the gram‐scale preparation of an intermediate en route to the FDA‐approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol." @default.
- W2938874913 created "2019-04-25" @default.
- W2938874913 creator A5014726663 @default.
- W2938874913 creator A5040327519 @default.
- W2938874913 creator A5040960219 @default.
- W2938874913 creator A5060412574 @default.
- W2938874913 date "2019-05-20" @default.
- W2938874913 modified "2023-10-16" @default.
- W2938874913 title "<i>meta</i>‐Nitration of Arenes Bearing <i>ortho</i>/<i>para</i> Directing Group(s) Using C−H Borylation" @default.
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- W2938874913 doi "https://doi.org/10.1002/chem.201901633" @default.
- W2938874913 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30974007" @default.