Palladium-catalyzed cross-coupling reactions with fluorinated substrates: Mechanistic insights into the undesired hydrodehalogenation of aryl halides

Meital Orbach; Joyanta Choudhury; Michal Lahav; Olena V. Zenkina; Yael Diskin-Posner; Gregory Leitus; Mark A. Iron; Milko E. Van Der Boom

doi:10.1021/om200898t

Palladium-catalyzed cross-coupling reactions with fluorinated substrates: Mechanistic insights into the undesired hydrodehalogenation of aryl halides

Meital Orbach, Joyanta Choudhury, Michal Lahav, Olena V. Zenkina, Yael Diskin-Posner, Gregory Leitus, Mark A. Iron, Milko E. Van Der Boom

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article

11 Citations (Scopus)

Abstract

We report here that the undesired hydrodehalogenation in cross-coupling reactions with fluorinated substrates involves water as a possible hydrogen source. Moreover, the product distribution (hydrodehalogenation vs carbon-carbon coupling) can be controlled by varying the phosphine substituents. Significant hydrodehalogenation occurs prior to the formation of Ar _F-Pd(II)-Br complexes. DFT calculations were used to evaluate a direct hydrodehalogenation route with a phosphine and water. These findings provide new mechanistic insight into aryl-Br bond activation with fluorinated substrates and selective arene functionalization.

Original language	English
Pages (from-to)	1271-1274
Number of pages	4
Journal	Organometallics
Volume	31
Issue number	4
DOIs	https://doi.org/10.1021/om200898t
Publication status	Published - Feb 27 2012

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ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Cite this

Orbach, M., Choudhury, J., Lahav, M., Zenkina, O. V., Diskin-Posner, Y., Leitus, G., Iron, M. A., & Van Der Boom, M. E. (2012). Palladium-catalyzed cross-coupling reactions with fluorinated substrates: Mechanistic insights into the undesired hydrodehalogenation of aryl halides. Organometallics, 31(4), 1271-1274. https://doi.org/10.1021/om200898t

Palladium-catalyzed cross-coupling reactions with fluorinated substrates : Mechanistic insights into the undesired hydrodehalogenation of aryl halides. / Orbach, Meital; Choudhury, Joyanta; Lahav, Michal; Zenkina, Olena V.; Diskin-Posner, Yael; Leitus, Gregory; Iron, Mark A.; Van Der Boom, Milko E.

In: Organometallics, Vol. 31, No. 4, 27.02.2012, p. 1271-1274.

Research output: Contribution to journal › Article

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10.1021/om200898t