Phenol-Tethered N-Heterocyclic Benzimidazol-2-ylidene Carbene Interactions with the Early Lanthanides

Jacob P. Brannon; Jeri Goldberg; Jennalyn Branson; Joseph M. Sperling; Cristian Celis-Barros; Thomas E. Albrecht-Schönzart

doi:10.1021/acs.organomet.3c00041

Phenol-Tethered N-Heterocyclic Benzimidazol-2-ylidene Carbene Interactions with the Early Lanthanides

Jacob P. Brannon, Jeri Goldberg, Jennalyn Branson, Joseph M. Sperling, Cristian Celis-Barros, Thomas E. Albrecht-Schönzart

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

The cyclization of salophan with triethyl orthoformate in the presence of HBr results in a bisphenol benzimidazolium carbene precursor 1,3-bis(2-hydroxybenzyl)-2H-benzimidazolium bromide (H₃OBBIm). By reacting H₃OBBIm in a one-pot synthesis with Ln(N(SiMe₃)₂)₃ (Ln = La-Sm excl. Pm) and an excess of KN(SiMe₃)₂, the N-heterocyclic carbene (NHC) complexes, [Ln(OBBIm)₂(N″)][K₂THF_x], can be prepared and isolated. These complexes were characterized by single-crystal X-ray diffraction, solution- and solid-state UV-vis-near-infrared spectroscopy, and ¹H NMR. These complexes possess distorted pentagonal bipyramid geometries.

Original language	English
Pages (from-to)	1477-1486
Number of pages	10
Journal	Organometallics
Volume	42
Issue number	13
DOIs	https://doi.org/10.1021/acs.organomet.3c00041
State	Published - Jul 10 2023
Externally published	Yes

Funding

This work was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Heavy Elements Chemistry program, under award number DE-FG02-13ER16414.

Funders	Funder number
U.S. Department of Energy
Office of Science
Basic Energy Sciences	DE-FG02-13ER16414

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10.1021/acs.organomet.3c00041

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title = "Phenol-Tethered N-Heterocyclic Benzimidazol-2-ylidene Carbene Interactions with the Early Lanthanides",

abstract = "The cyclization of salophan with triethyl orthoformate in the presence of HBr results in a bisphenol benzimidazolium carbene precursor 1,3-bis(2-hydroxybenzyl)-2H-benzimidazolium bromide (H3OBBIm). By reacting H3OBBIm in a one-pot synthesis with Ln(N(SiMe3)2)3 (Ln = La-Sm excl. Pm) and an excess of KN(SiMe3)2, the N-heterocyclic carbene (NHC) complexes, [Ln(OBBIm)2(N″)][K2THFx], can be prepared and isolated. These complexes were characterized by single-crystal X-ray diffraction, solution- and solid-state UV-vis-near-infrared spectroscopy, and 1H NMR. These complexes possess distorted pentagonal bipyramid geometries.",

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AU - Brannon, Jacob P.

AU - Goldberg, Jeri

AU - Branson, Jennalyn

AU - Sperling, Joseph M.

AU - Celis-Barros, Cristian

AU - Albrecht-Schönzart, Thomas E.

PY - 2023/7/10

Y1 - 2023/7/10

N2 - The cyclization of salophan with triethyl orthoformate in the presence of HBr results in a bisphenol benzimidazolium carbene precursor 1,3-bis(2-hydroxybenzyl)-2H-benzimidazolium bromide (H3OBBIm). By reacting H3OBBIm in a one-pot synthesis with Ln(N(SiMe3)2)3 (Ln = La-Sm excl. Pm) and an excess of KN(SiMe3)2, the N-heterocyclic carbene (NHC) complexes, [Ln(OBBIm)2(N″)][K2THFx], can be prepared and isolated. These complexes were characterized by single-crystal X-ray diffraction, solution- and solid-state UV-vis-near-infrared spectroscopy, and 1H NMR. These complexes possess distorted pentagonal bipyramid geometries.

AB - The cyclization of salophan with triethyl orthoformate in the presence of HBr results in a bisphenol benzimidazolium carbene precursor 1,3-bis(2-hydroxybenzyl)-2H-benzimidazolium bromide (H3OBBIm). By reacting H3OBBIm in a one-pot synthesis with Ln(N(SiMe3)2)3 (Ln = La-Sm excl. Pm) and an excess of KN(SiMe3)2, the N-heterocyclic carbene (NHC) complexes, [Ln(OBBIm)2(N″)][K2THFx], can be prepared and isolated. These complexes were characterized by single-crystal X-ray diffraction, solution- and solid-state UV-vis-near-infrared spectroscopy, and 1H NMR. These complexes possess distorted pentagonal bipyramid geometries.

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JF - Organometallics

IS - 13

ER -

Phenol-Tethered N-Heterocyclic Benzimidazol-2-ylidene Carbene Interactions with the Early Lanthanides

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