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Perkowski AJ, Cruz CL, Nicewicz DA. Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis. J Am Chem Soc. 2015;137(50):15684-7doi: 10.1021/jacs.5b11800.
Perkowski, A. J., Cruz, C. L., & Nicewicz, D. A. (2015). Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis. Journal of the American Chemical Society, 137(50), 15684-7. https://doi.org/10.1021/jacs.5b11800
Perkowski, Andrew J, et al. "Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis." Journal of the American Chemical Society vol. 137,50 (2015): 15684-7. doi: https://doi.org/10.1021/jacs.5b11800
Perkowski AJ, Cruz CL, Nicewicz DA. Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis. J Am Chem Soc. 2015 Dec 23;137(50):15684-7. doi: 10.1021/jacs.5b11800. Epub 2015 Dec 11. PMID: 26645387.
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J Am Chem Soc. 2015 Dec 23;137(50):15684-7. doi: 10.1021/jacs.5b11800. Epub 2015 Dec 11.

Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis.

Journal of the American Chemical Society

Andrew J Perkowski, Cole L Cruz, David A Nicewicz

Affiliations

  1. Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.

PMID: 26645387 DOI: 10.1021/jacs.5b11800

Abstract

The Newman-Kwart rearrangement is perhaps the quintessential method for the synthesis of thiophenols from the corresponding phenol. However, the high thermal conditions required for the rearrangement of the requisite O-aryl carbamothioates often leads to decomposition. Herein, we present a general strategy for catalysis of O-aryl carbamothioates to S-aryl carbamothioates using catalytic quantities of a commercially available organic single-electron photooxidant. Importantly, this reaction is facilitated at ambient temperatures.

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