Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne
Abstract
A low-spin and mononuclear vanadium complex, (Menacnac)V(CO)(η2-P≡CtBu) (2) (Menacnac-=[ArNC(CH3)]2CH, Ar=2,6-iPr2C6H3), was prepared upon treatment of the vanadium neopentylidyne complex (Menacnac)V≡CtBu(OTf) (1) with Na(OCP)(diox)2.5 (diox=1,4-dioxane), while the isoelectronic ate-complex [Na(15-crown-5)]{([ArNC(CH2)]CH[C(CH3)NAr])V(CO)(η2-P≡CtBu)} (4), was obtained via the reaction of Na(OCP)(diox)2.5 and ([ArNC(CH2)]CH[C(CH3)NAr])V≡CtBu(OEt2) (3) in the presence of crown-ether. Computational studies suggest that the P-atom transfer proceeds by [2+2]-cycloaddition of the P≡C bond across the V≡CtBu moiety, followed by a reductive decarbonylation to form the V-C≡O linkage. Additionally, the nature of the electronic ground state in diamagnetic complexes, 2 and 4, was further investigated both theoretically and experimentally, using a combination of density functional theory (DFT) calculations, UV/Vis and NMR spectroscopies, cyclic voltammetry, X-ray absorption spectroscopy (XAS) measurements, and comparison of salient bond metrics derived from X-ray single-crystal structural characterization. In combination, these data are consistent with a low-valent vanadium ion in complexes 2 and 4. This study represents the first example of a metathesis reaction between the P-atom of [PCO]- and an alkylidyne ligand.
- Authors:
-
[1];
[2];
[3];
[1];
[1];
[4];
[4];
[4];
[2];
[1]
- Univ. of Pennsylvania, Philadelphia, PA (United States)
- Inst. for Basic Science (IBS) Daejeon (South Korea). Center for Catalytic Hydrocarbon Functionalizations; Korea Advanced Inst. Science and Technology (KAIST), Daejeon (South Korea)
- Inst. for Basic Science (IBS) Daejeon (South Korea). Center for Catalytic Hydrocarbon Functionalizations
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- National Science Foundation (NSF); National Institutes of Health (NIH); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
- OSTI Identifier:
- 1845329
- Grant/Contract Number:
- AC02-06CH11357; CHE-0848248; CHE-1152123; 3R01GM118510-03S1; 3R01GM087605-06S1
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie
- Additional Journal Information:
- Journal Volume: 133; Journal Issue: 46; Journal ID: ISSN 0044-8249
- Publisher:
- German Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; diketeiminate; phosphaalkyne; phosphaethynolate; phosphorus; vanadium; alkylidyne
Citation Formats
Jafari, Mehrafshan G., Park, Yerin, Pudasaini, Bimal, Kurogi, Takashi, Carroll, Patrick J., Kaphan, David M., Kropf, Jeremy, Delferro, Massimiliano, Baik, Mu‐Hyun, and Mindiola, Daniel J. Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne. United States: N. p., 2021.
Web. doi:10.1002/ange.202107475.
Jafari, Mehrafshan G., Park, Yerin, Pudasaini, Bimal, Kurogi, Takashi, Carroll, Patrick J., Kaphan, David M., Kropf, Jeremy, Delferro, Massimiliano, Baik, Mu‐Hyun, & Mindiola, Daniel J. Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne. United States. https://doi.org/10.1002/ange.202107475
Jafari, Mehrafshan G., Park, Yerin, Pudasaini, Bimal, Kurogi, Takashi, Carroll, Patrick J., Kaphan, David M., Kropf, Jeremy, Delferro, Massimiliano, Baik, Mu‐Hyun, and Mindiola, Daniel J. Thu .
"Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne". United States. https://doi.org/10.1002/ange.202107475. https://www.osti.gov/servlets/purl/1845329.
@article{osti_1845329,
title = {Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne},
author = {Jafari, Mehrafshan G. and Park, Yerin and Pudasaini, Bimal and Kurogi, Takashi and Carroll, Patrick J. and Kaphan, David M. and Kropf, Jeremy and Delferro, Massimiliano and Baik, Mu‐Hyun and Mindiola, Daniel J.},
abstractNote = {A low-spin and mononuclear vanadium complex, (Menacnac)V(CO)(η2-P≡CtBu) (2) (Menacnac-=[ArNC(CH3)]2CH, Ar=2,6-iPr2C6H3), was prepared upon treatment of the vanadium neopentylidyne complex (Menacnac)V≡CtBu(OTf) (1) with Na(OCP)(diox)2.5 (diox=1,4-dioxane), while the isoelectronic ate-complex [Na(15-crown-5)]{([ArNC(CH2)]CH[C(CH3)NAr])V(CO)(η2-P≡CtBu)} (4), was obtained via the reaction of Na(OCP)(diox)2.5 and ([ArNC(CH2)]CH[C(CH3)NAr])V≡CtBu(OEt2) (3) in the presence of crown-ether. Computational studies suggest that the P-atom transfer proceeds by [2+2]-cycloaddition of the P≡C bond across the V≡CtBu moiety, followed by a reductive decarbonylation to form the V-C≡O linkage. Additionally, the nature of the electronic ground state in diamagnetic complexes, 2 and 4, was further investigated both theoretically and experimentally, using a combination of density functional theory (DFT) calculations, UV/Vis and NMR spectroscopies, cyclic voltammetry, X-ray absorption spectroscopy (XAS) measurements, and comparison of salient bond metrics derived from X-ray single-crystal structural characterization. In combination, these data are consistent with a low-valent vanadium ion in complexes 2 and 4. This study represents the first example of a metathesis reaction between the P-atom of [PCO]- and an alkylidyne ligand.},
doi = {10.1002/ange.202107475},
journal = {Angewandte Chemie},
number = 46,
volume = 133,
place = {United States},
year = {Thu Oct 07 00:00:00 EDT 2021},
month = {Thu Oct 07 00:00:00 EDT 2021}
}
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