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Selective ortho C-H Activation of Pyridines Directed by Lewis Acidic Boron of PBP Pincer Iridium Complexes.

Authors :
Wei-Chun Shih
Ozerov, Oleg V.
Source :
Journal of the American Chemical Society. 12/6/2017, Vol. 139 Issue 48, p17297-17300. 4p.
Publication Year :
2017

Abstract

Transition-metal mediated C-H functionalization has emerged as a powerful method in the chemistry relevant to the synthesis of pharmaceuticals, agrochemicals, and advanced materials. Because organic molecules typically contain multiple types of C-H bonds, selective C-H functionalization is a major ongoing challenge. C-H activation of heteroatom-containing organics has often been approached via the use of the directing effect, whereby the coordination to the basic heteroatom directs the reactive metal center to a specific C-H bond. We now report a different approach where the nitrogen donor in pyridine derivatives coordinates to an ancillary Lewis acidic boryl ligand directly attached to the metal (iridium) center, as opposed to the metal itself. This topology directs the iridium center to activate a different C-H bond than in the cases of directing donor coordination to the metal. Using this strategy, we demonstrate ortho-regiospecific C-H activation of pyridines and an example of the subsequent functionalization via C-C bond formation. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00027863
Volume :
139
Issue :
48
Database :
Academic Search Index
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
126761841
Full Text :
https://doi.org/10.1021/jacs.7b10570