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Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation

Murray, Alexander T., Surendranath, Yogesh (2017) Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation. ACS Catalysis, 7 (5). pp. 3307-3312. ISSN 2155-5435. (doi:10.1021/acscatal.7b00395) (KAR id:67392)

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https://dx.doi.org/10.1021/acscatal.7b00395

Abstract

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.

Item Type: Article
DOI/Identification number: 10.1021/acscatal.7b00395
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences
Depositing User: Alexander Murray
Date Deposited: 22 Jun 2018 09:18 UTC
Last Modified: 13 Jan 2020 12:03 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/67392 (The current URI for this page, for reference purposes)
Murray, Alexander T.: https://orcid.org/0000-0002-7914-8205
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