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Synthesis 2018; 50(24): 4875-4882
DOI: 10.1055/s-0037-1610240
DOI: 10.1055/s-0037-1610240
paper
Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel
This work was supported by NIH R01EB014354, R01DC014461, and NSF DMR-1506613. Spectra were obtained with instrumentation supported by NIH grants P20GM104316, P30GM110758, S10RR026962, S10OD016267 and NSF grants CHE-0840401, CHE-1229234, and CHE-1048367.Further Information
Publication History
Received: 19 July 2018
Accepted after revision: 20 July 2018
Publication Date:
20 August 2018 (online)
‡ These authors contributed equally
Abstract
Functionalized trans-cyclooctenes are useful bioorthogonal reagents that are typically prepared using a flow photoisomerization method in which the product is captured by AgNO3 on silica gel. While this method is effective, the leaching of silver can be problematic when scaling up syntheses. It is shown here that Ag(I) immobilized on tosic silica gel can be used to capture trans-cyclooctene products at higher loadings without leaching. It is demonstrated that the sulfonated silica gel can be regenerated and reused with similar yields over multiple runs. Nine different trans-cyclooctenes were synthesized, including those commonly utilized in bioorthogonal chemistry as well as new amine and carboxylic acid derivatives.
Supporting Information
- Copies of 1H NMR and 13C NMR spectra are provided. Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610240.
- Supporting Information
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