Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation
Commercially available carbon blacks serve as effective metal-free catalysts for the selective hydrogenation of carbon–carbon multiple bonds under aerobic conditions using hydrazine as the terminal reductant. The reaction, which proceeds through a putative diimide intermediate, displays high toleran...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/115122 https://orcid.org/0000-0003-1016-3420 |
| _version_ | 1826208184677695488 |
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| author | Murray, Alexander T Surendranath, Yogesh |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Murray, Alexander T Surendranath, Yogesh |
| author_sort | Murray, Alexander T |
| collection | MIT |
| description | Commercially available carbon blacks serve as effective metal-free catalysts for the selective hydrogenation of carbon–carbon multiple bonds under aerobic conditions using hydrazine as the terminal reductant. The reaction, which proceeds through a putative diimide intermediate, displays high tolerance to a variety of functional groups, including those sensitive to nucleophilic displacement by hydrazine, aerobic oxidation, or hydrazine-mediated reduction. Hydrazine chemisorbs strongly to the carbon surface, attenuating its native oxidative reactivity and allowing for selective hydrogenation. The catalytic sequence established here effectively umpolungs the reactivity of carbon, thereby enabling the use of this low-cost material in selective reduction catalysis. Keywords: alkene; carbocatalysis; carbon black; diimide; hydrogenation |
| first_indexed | 2024-09-23T14:01:50Z |
| format | Article |
| id | mit-1721.1/115122 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T14:01:50Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1151222022-10-01T18:42:02Z Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation Murray, Alexander T Surendranath, Yogesh Massachusetts Institute of Technology. Department of Chemistry Surendranath, Yogesh Murray, Alexander T Surendranath, Yogesh Commercially available carbon blacks serve as effective metal-free catalysts for the selective hydrogenation of carbon–carbon multiple bonds under aerobic conditions using hydrazine as the terminal reductant. The reaction, which proceeds through a putative diimide intermediate, displays high tolerance to a variety of functional groups, including those sensitive to nucleophilic displacement by hydrazine, aerobic oxidation, or hydrazine-mediated reduction. Hydrazine chemisorbs strongly to the carbon surface, attenuating its native oxidative reactivity and allowing for selective hydrogenation. The catalytic sequence established here effectively umpolungs the reactivity of carbon, thereby enabling the use of this low-cost material in selective reduction catalysis. Keywords: alkene; carbocatalysis; carbon black; diimide; hydrogenation United States. Department of Energy. Office of Basic Energy Sciences (Award DE-SC0014176) 2018-05-01T14:22:58Z 2018-05-01T14:22:58Z 2017-03 2017-02 Article http://purl.org/eprint/type/JournalArticle 2155-5435 2155-5435 http://hdl.handle.net/1721.1/115122 Murray, Alexander T. and Yogesh Surendranath. “Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation.” ACS Catalysis 7, 5 (April 2017): 3307–3312 © 2017 American Chemical Society https://orcid.org/0000-0003-1016-3420 en_US http://dx.doi.org/10.1021/acscatal.7b00395 ACS Catalysis Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Surendranath via Erja Kajosalo |
| spellingShingle | Murray, Alexander T Surendranath, Yogesh Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title | Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title_full | Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title_fullStr | Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title_full_unstemmed | Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title_short | Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation |
| title_sort | reversing the native aerobic oxidation reactivity of graphitic carbon heterogeneous metal free alkene hydrogenation |
| url | http://hdl.handle.net/1721.1/115122 https://orcid.org/0000-0003-1016-3420 |
| work_keys_str_mv | AT murrayalexandert reversingthenativeaerobicoxidationreactivityofgraphiticcarbonheterogeneousmetalfreealkenehydrogenation AT surendranathyogesh reversingthenativeaerobicoxidationreactivityofgraphiticcarbonheterogeneousmetalfreealkenehydrogenation |