Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes
Abstract
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51–89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48–97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
Main Authors
Format
Articles
Research article
Published
2018
Series
Subjects
Publication in research information system
Publisher
American Chemical Society
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-201802211552Use this for linking
Review status
Peer reviewed
ISSN
0022-3263
DOI
https://doi.org/10.1021/acs.joc.7b02896
Language
English
Published in
Journal of Organic Chemistry
Citation
- Vale, J. R., Rimpiläinen, T., Sievänen, E., Rissanen, K., Afonso, C. A. M., & Candeias, N. R. (2018). Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes. Journal of Organic Chemistry, 83(4), 1948-1958. https://doi.org/10.1021/acs.joc.7b02896
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Copyright© 2018 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by American Chemical Society. Published in this repository with the kind permission of the publisher.