Compartmentalization of incompatible reagents within Pickering emulsion droplets for one-pot cascade reactions

Yang, Hengquan; Fu, Luman; Wei, Lijuan; Liang, Jifen; Binks, Bernard P.

Abstract

It is a dream that future synthetic chemistry can mimic living systems to process multistep cascade reactions in a one-pot fashion. One of the key challenges is the mutual destruction of incompatible or opposing reagents, for example, acid and base, oxidants and reductants. A conceptually novel strategy is developed here to address this challenge. This strategy is based on a layered Pickering emulsion system, which is obtained through lamination of Pickering emulsions. In this working Pickering emulsion, the dispersed phase can separately compartmentalize the incompatible reagents to avoid their mutual destruction, while the continuous phase allows other reagent molecules to diffuse freely to access the compartmentalized reagents for chemical reactions. The compartmentalization effects and molecular transport ability of the Pickering emulsion were investigated. The deacetalization–reduction, deacetalization–Knoevenagel, deacetalization–Henry and diazotization–iodization cascade reactions demonstrate well the versatility and flexibility of our strategy in processing the one-pot cascade reactions involving mutually destructive reagents.

Citation

Yang, H., Fu, L., Wei, L., Liang, J., & Binks, B. P. (2015). Compartmentalization of incompatible reagents within Pickering emulsion droplets for one-pot cascade reactions. Journal of the American Chemical Society, 137(3), 1362-1371. https://doi.org/10.1021/ja512337z

• Journal Article Type: Article
• Acceptance Date: Dec 3, 2014
• Online Publication Date: Dec 30, 2014
• Publication Date: Jan 20, 2015
• Deposit Date: Mar 15, 2016
• Publicly Available Date: Mar 15, 2016
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 137
• Issue: 3
• Pages: 1362-1371
• DOI: https://doi.org/10.1021/ja512337z
• Keywords: Pickering emulsion droplets, One-pot cascade reactions
• Public URL: https://hull-repository.worktribe.com/output/412978
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/ja512337z
• Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see DOI: 10.1021/ja512337z .
• Contract Date: Mar 15, 2016