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Quantification of Catalytic Activity for Electrostatically Enhanced Thioureas via Reaction Kinetics and UV-vis Spectroscopic Measurement.

The Journal of organic chemistry (2018-07-20)
Yang Fan, Curtis Payne, Steven R Kass
ABSTRACT

Charged thiourea derivatives containing one and two methylated or octylated pyridinium ion centers and a tetraarylborate or triflate counteranion are reported. These novel catalysts are much more active in the Friedel-Crafts reactions of trans-β-nitroalkenes with N-methylindoles than the privileged N, N'-bis(3,5-bis(trifluoromethyl)phenyl)thiourea (i.e., Schreiner's thiourea) by up to 2-3 orders of magnitude. A previously reported UV-vis spectroscopic method by Kozlowski et al. was exploited to rationalize their reactivity order along with noncharged analogues. These results offer a new design strategy for organocatalysts by introducing positively charged centers without adding additional N-H, O-H, or S-H hydrogen bond donor sites.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
7-Methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one, ≥95%

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