Reversing the Native Aerobic Oxidation Reactivity of Graphitic Carbon: Heterogeneous Metal-Free Alkene Hydrogenation
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Author(s)
Murray, Alexander T
Surendranath, Yogesh
Date Issued
March 2017
Journal
ACS Catalysis
Publisher
American Chemical Society (ACS)
Citation
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
Version
Author's final manuscript
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. Keywords: alkene; carbocatalysis; carbon black; diimide; hydrogenation
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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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.
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DOI of Published Version
https://doi.org/10.1021/acscatal.7b00395
