DOI: 10.1039/C7GC03437G, Communication
An aniline/acid-catalyzed method for constructing thiophenes 2 from inexpensive ketones 1 and elemental sulfur is reported.
Sulfurative self-condensation of ketones and elemental sulfur: a three-component access to thiophenes catalyzed by aniline acid–base conjugate pairs
Abstract
A sulfurative self-condensation method for constructing thiophenes 2 by a reaction between ketones 1 and elemental sulfur is reported. This reaction, which is catalyzed by anilines and their salts with strong acids, starts from readily available and inexpensive materials, and releases only water as a by-product.
2,4-Di-p-tolylthiophene (2b)2
2 M. Arisawa, T. Ichikawa, and M. Yamaguchi, Chem. Commun. 2015, 51, 8821
Eluent heptane:toluene 9:1. 190 mg, 72%.
1 H NMR (300 MHz, CDCl3) δ 7.60-7.54 (m, 5H), 7.34 (s, 1H), 7.27-7.23 (m, 4H), 2.42 (s, 6H).
13C NMR (75 MHz, CDCl3) δ 145.3, 143.3, 137.8, 137.2, 133.5, 131.9, 129.9, 129.8, 126.5, 126.0, 122.1, 118.9, 21.5, 21.5.
Binh Thanh Nguyen
CV Binh Nguyen
CNRS Research Associate CR1 ( ORCID , ResearchGate )
ICSN-CNRS Bât. 27
1, avenue de la Terrasse
91190 Gif-sur-Yvette France
thanh-binh.nguyen_at_cnrs.fr
+33 1 69 82 45 49
Education and work experience2015: Habilitation to Direct Research (HDR)
2011 – present: CNRS research associate at ICSN – Paris-Saclay University
2009 – 2011: Post-doctoral Fellow at ICSN (Dr. Françoise Guéritte and Dr. Qian Wang)
2003 – 2006: Ph.D. student at the UCO2M Organic Synthesis Laboratory (University of Maine, Le Mans, France, Dr. Gilles Dujardin, Dr. Arnaud Martel, Professor Robert Dhal)
Research Interests
Green chemistry (Atom, step and redox economic transformation), green synthetic tools: O2, S8, photochemistry, iron catalyst
Elemental sulfur as a synthetic tool (building block, oxidant, reductant, catalyst)
Iron-sulfur catalysts
Heterocycle synthesis
Scientific Communications
47 publications
Selected recent publications ( complete list )
[1] Adv. Synth. Catal. 2017 , 359 , 1106.
[2] Asian J. Org. Chem. 2017 , 6 , 477.
[3] Org. Lett. 2016 , 18 , 2177.
[4] Org. Process Res. Dev. 2016 , 20 , 319.
[5] Angew. Chem. Int. Ed. 2014 , 53 , 13808.
[6] J. Am. Chem. Soc. 2013 , 135 , 118.
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