Journal
TETRAHEDRON LETTERS
Volume 86, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153499
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Funding
- University at Albany, State University of New York
- National Science Foundation [MRI 1726724, CHE 1710174]
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A visible-light-mediated thiol-ene reaction in aqueous medium is successfully achieved, with two different reaction pathways discovered in acidic and basic buffer systems, suitable for unprotected peptides.
A visible-light-mediated thiol-ene reaction is successfully operated in aqueous medium. An organic photoredox catalyst (9-mesityl-10-methylacridinum tetrafluoroborate) is used to initiate the radical process to generate thiyl radicals upon light irradiation. Two reaction pathways were discovered in different aqueous buffer systems. A thiol-ene adduct is preferred in acidic reaction medium; while disulfide formation is found to be favored in basic reaction medium. The photocatalytic method is demonstrated to be applicable on unprotected peptides. (C) 2021 Elsevier Ltd. All rights reserved.
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