Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands Article Swipe
Yuyang Dong
,
Colton J. Lund
,
Gerard J. Porter
,
Ryan M. Clarke
,
Shao‐Liang Zheng
,
Thomas R. Cundari
,
Theodore A. Betley
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.0c09839
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.0c09839
The trityl-substituted bisoxazoline (TrHBOX) was prepared as a chiral analogue to a previously reported nickel dipyrrin system capable of ring-closing amination catalysis. Ligand metalation with divalent NiI2(py)4 followed by potassium graphite reduction afforded the monovalent (TrHBOX)Ni(py) (4). Slow addition of 1.4 equiv of a benzene solution of 1-adamantylazide to 4 generated the tetrazido (TrHBOX)Ni(κ2-N4Ad2) (5) and terminal iminyl adduct (TrHBOX)Ni(NAd) (6). Investigation of 6 via single-crystal X-ray crystallography, NMR and EPR spectroscopies, and computations revealed a Ni(II)-iminyl radical formulation, similar to its dipyrrinato congener. Complex 4 exhibits enantioselective intramolecular C-H bond amination to afford N-heterocyclic products from 4-aryl-2-methyl-2-azidopentanes. Catalytic C-H amination occurs under mild conditions (5 mol % catalyst, 60 °C) and provides pyrrolidine products in decent yield (29%-87%) with moderate ee (up to 73%). Substrates with a 3,5-dialkyl substitution on the 4-aryl position maximized the observed enantioselectivity. Kinetic studies to probe the reaction mechanism were conducted using 1H and 19F NMR spectroscopies. A small, intermolecular kinetic isotope effect (1.35 ± 0.03) suggests an H-atom abstraction step with an asymmetric transition state while the reaction rate is measured to be first order in catalyst and zeroth order in substrate concentrations. Enantiospecific deuterium labeling studies show that the enantioselectivity is dictated by both the H-atom abstraction and radical recombination steps due to the comparable rate between radical rotation and C-N bond formation. Furthermore, the competing elements of the two-step reaction where H-removal from the pro-R configuration is preferred while the preferential radical capture occurs with the Si face of the carboradical likely lead to the diminished ee observed, as corroborated by theoretical calculations. Based on these enantio-determining steps, catalytic enantioselective synthesis of 2,5-bis-tertiary pyrrolidines is demonstrated with good yield (50-78%) and moderate ee (up to 79%).
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/jacs.0c09839
- OA Status
- green
- Cited By
- 75
- References
- 92
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3119706943
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W3119706943Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/jacs.0c09839Digital Object Identifier
- Title
-
Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) LigandsWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2021Year of publication
- Publication date
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2021-01-04Full publication date if available
- Authors
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Yuyang Dong, Colton J. Lund, Gerard J. Porter, Ryan M. Clarke, Shao‐Liang Zheng, Thomas R. Cundari, Theodore A. BetleyList of authors in order
- Landing page
-
https://doi.org/10.1021/jacs.0c09839Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
- OA URL
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https://www.osti.gov/biblio/1831108Direct OA link when available
- Concepts
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Chemistry, Amination, Enantioselective synthesis, Medicinal chemistry, Pyrrolidine, Catalysis, Aryl, Stereochemistry, Ligand (biochemistry), Intramolecular force, Organic chemistry, Biochemistry, Alkyl, ReceptorTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
75Total citation count in OpenAlex
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2025: 12, 2024: 11, 2023: 15, 2022: 18, 2021: 18Per-year citation counts (last 5 years)
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92Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.dipyrrinato | 82 |
| abstract_inverted_index.pyrrolidine | 113 |
| abstract_inverted_index.theoretical | 260 |
| abstract_inverted_index.<i>pro</i>-R | 233 |
| abstract_inverted_index.Furthermore, | 221 |
| abstract_inverted_index.bisoxazoline | 2 |
| abstract_inverted_index.carboradical | 249 |
| abstract_inverted_index.computations | 73 |
| abstract_inverted_index.corroborated | 258 |
| abstract_inverted_index.demonstrated | 274 |
| abstract_inverted_index.formulation, | 78 |
| abstract_inverted_index.preferential | 239 |
| abstract_inverted_index.pyrrolidines | 272 |
| abstract_inverted_index.ring-closing | 19 |
| abstract_inverted_index.substitution | 129 |
| abstract_inverted_index.<sup>1</sup>H | 148 |
| abstract_inverted_index.Investigation | 61 |
| abstract_inverted_index.Ni(II)-iminyl | 76 |
| abstract_inverted_index.calculations. | 261 |
| abstract_inverted_index.configuration | 234 |
| abstract_inverted_index.recombination | 207 |
| abstract_inverted_index.<sup>19</sup>F | 150 |
| abstract_inverted_index.intermolecular | 155 |
| abstract_inverted_index.intramolecular | 88 |
| abstract_inverted_index.single-crystal | 65 |
| abstract_inverted_index.Enantiospecific | 190 |
| abstract_inverted_index.concentrations. | 189 |
| abstract_inverted_index.spectroscopies, | 71 |
| abstract_inverted_index.spectroscopies. | 152 |
| abstract_inverted_index.1-adamantylazide | 47 |
| abstract_inverted_index.2,5-bis-tertiary | 271 |
| abstract_inverted_index.crystallography, | 67 |
| abstract_inverted_index.enantioselective | 87, 268 |
| abstract_inverted_index.enantioselectivity | 197 |
| abstract_inverted_index.trityl-substituted | 1 |
| abstract_inverted_index.(<sup>TrH</sup>BOX) | 3 |
| abstract_inverted_index.enantio-determining | 265 |
| abstract_inverted_index.enantioselectivity. | 137 |
| abstract_inverted_index.<i>N</i>-heterocyclic | 94 |
| abstract_inverted_index.(<sup>TrH</sup>BOX)Ni(py) | 35 |
| abstract_inverted_index.(<sup>TrH</sup>BOX)Ni(NAd) | 59 |
| abstract_inverted_index.NiI<sub>2</sub>(py)<sub>4</sub> | 26 |
| abstract_inverted_index.4-aryl-2-methyl-2-azidopentanes. | 97 |
| abstract_inverted_index.(<sup>TrH</sup>BOX)Ni(κ<sup>2</sup>-N<sub>4</sub>Ad<sub>2</sub>) | 53 |
| cited_by_percentile_year.max | 100 |
| cited_by_percentile_year.min | 89 |
| corresponding_author_ids | https://openalex.org/A5022569799 |
| countries_distinct_count | 1 |
| institutions_distinct_count | 7 |
| corresponding_institution_ids | https://openalex.org/I136199984 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/6 |
| sustainable_development_goals[0].score | 0.6000000238418579 |
| sustainable_development_goals[0].display_name | Clean water and sanitation |
| citation_normalized_percentile.value | 0.97923477 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | True |