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

Yang Fan, Curtis Payne, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)10855-10863
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number18
DOIs
StatePublished - Sep 21 2018

Bibliographical note

Funding Information:
Generous support from the National Science Foundation (CHE-1665392) the Petroleum Research Fund (55631-ND4) as administered by the American Chemical Society, and the Minnesota Supercomputer Institute for Advanced Computational Research are gratefully acknowledged.

Publisher Copyright:
Copyright © 2018 American Chemical Society.

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