Journal
TETRAHEDRON LETTERS
Volume 56, Issue 30, Pages 4434-4437Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.04.079
Keywords
Cu(I); Ligand design; Bifunctional; Indicator; Conjugate addition
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Funding
- National Science Foundation [CHE-1012897]
- University of New Hampshire Dissertation Year Fellowship
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Herein we report an efficient eight-step synthesis of N-1-(3-(methylthio)propyl)-2-((3-(methylthio)propyl)thio)benzene-1,4-diamine (1) from 6-nitrobenzo[d]thiazole. Incorporation of a nitro rather than a hydroxyl functionality off the aromatic ring serves to enhance conversion during thia- and aza-conjugate additions. Ultimate reduction of the nitro substituent affords a bifunctional Cu(I) chelate in gram-scale quantities for subsequent sensing applications. (C) 2015 Elsevier Ltd. All rights reserved.
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