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Title: C–H Activation of Pyrazolyl Ligands by Ru(II)

Abstract

Previously, hydridotris(pyrazolyl)borate (Tp) Ru(II) alkyl and aryl complexes of the type TpRu(L)(NCMe)R (R = methyl or aryl; L = charge-neutral two-electron donating ligand) were demonstrated to activate aromatic C–H bonds. To confirm the impact of replacing the anionic Tp ligand with charge-neutral poly(pyrazolyl)alkane ligands, [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] (pz = pyrazolyl, BAr'4 = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) was prepared. Heating a C6D6 solution of [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] with 1 equiv of NCMe resulted in C–H activation of the 5-position of a pyrazolyl ring to yield [(κ3-(N,C5,N)C(pz)4)Ru(P(OCH2)3CEt)(NCMe)2][BAr'4] and CH4. Intramolecular C–H activation of the 5-position of a pyrazolyl ring also occurred when (η6-p-cymene)Ru(P(OCH2)3CEt)(Br)Ph was heated in the presence of C(pz)4 to yield [(κ3-N,C5,N)C(pz)4]Ru(P(OCH2)3CEt)(NCMe)Br and C6H6. Density functional theory calculations showed that the different reactivities of TpRu(P(OCH2)3CEt)(NCMe)R and [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] result from the stronger binding of the Tp pyrazolyl rings to Ru(II) compared to that of C(pz)4

Authors:
 [1];  [1];  [1];  [2];  [1];  [3]
+ Show Author Affiliations
  1. Univ. of Virginia, Charlottesville, VA (United States)
  2. Univ. of North Texas, Denton, TX (United States)
  3. Univ. of Richmond, VA (United States)
Publication Date:
Research Org.:
Univ. of Virginia, Charlottesville, VA (United States); Univ. of North Texas, Denton, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1607835
Grant/Contract Number:  
SC0000776; FG02-03ER15387
Resource Type:
Accepted Manuscript
Journal Name:
Inorganic Chemistry
Additional Journal Information:
Journal Volume: 53; Journal Issue: 12; Journal ID: ISSN 0020-1669
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Joslin, Evan E., Quillian, Brandon, Gunnoe, T. Brent, Cundari, Thomas R., Sabat, Michal, and Myers, William H. C–H Activation of Pyrazolyl Ligands by Ru(II). United States: N. p., 2014. Web. doi:10.1021/ic500811n.
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Joslin, Evan E., Quillian, Brandon, Gunnoe, T. Brent, Cundari, Thomas R., Sabat, Michal, & Myers, William H. C–H Activation of Pyrazolyl Ligands by Ru(II). United States. https://doi.org/10.1021/ic500811n
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Joslin, Evan E., Quillian, Brandon, Gunnoe, T. Brent, Cundari, Thomas R., Sabat, Michal, and Myers, William H. Tue . "C–H Activation of Pyrazolyl Ligands by Ru(II)". United States. https://doi.org/10.1021/ic500811n. https://www.osti.gov/servlets/purl/1607835.
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@article{osti_1607835,
title = {C–H Activation of Pyrazolyl Ligands by Ru(II)},
author = {Joslin, Evan E. and Quillian, Brandon and Gunnoe, T. Brent and Cundari, Thomas R. and Sabat, Michal and Myers, William H.},
abstractNote = {Previously, hydridotris(pyrazolyl)borate (Tp) Ru(II) alkyl and aryl complexes of the type TpRu(L)(NCMe)R (R = methyl or aryl; L = charge-neutral two-electron donating ligand) were demonstrated to activate aromatic C–H bonds. To confirm the impact of replacing the anionic Tp ligand with charge-neutral poly(pyrazolyl)alkane ligands, [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] (pz = pyrazolyl, BAr'4 = tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) was prepared. Heating a C6D6 solution of [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] with 1 equiv of NCMe resulted in C–H activation of the 5-position of a pyrazolyl ring to yield [(κ3-(N,C5,N)C(pz)4)Ru(P(OCH2)3CEt)(NCMe)2][BAr'4] and CH4. Intramolecular C–H activation of the 5-position of a pyrazolyl ring also occurred when (η6-p-cymene)Ru(P(OCH2)3CEt)(Br)Ph was heated in the presence of C(pz)4 to yield [(κ3-N,C5,N)C(pz)4]Ru(P(OCH2)3CEt)(NCMe)Br and C6H6. Density functional theory calculations showed that the different reactivities of TpRu(P(OCH2)3CEt)(NCMe)R and [(C(pz)4)Ru(P(OCH2)3CEt)(NCMe)Me][BAr'4] result from the stronger binding of the Tp pyrazolyl rings to Ru(II) compared to that of C(pz)4},
doi = {10.1021/ic500811n},
journal = {Inorganic Chemistry},
number = 12,
volume = 53,
place = {United States},
year = {Tue May 27 00:00:00 EDT 2014},
month = {Tue May 27 00:00:00 EDT 2014}
}
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