Synthesis, Table of Contents Synthesis 2018; 50(24): 4875-4882DOI: 10.1055/s-0037-1610240 paper © Georg Thieme Verlag Stuttgart · New York Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel Ampofo Darko* a Department of Chemistry, University of Tennessee, Knoxville, TN, 37996, USA , Samantha J. Boyd b Department of Chemistry and Biochemistry, University of Delaware, Newark DE 19716, USA Email: jmfox@udel.edu , Joseph M. Fox* b Department of Chemistry and Biochemistry, University of Delaware, Newark DE 19716, USA Email: jmfox@udel.edu › Author Affiliations Recommend Article Abstract Buy Article All articles of this category ‡ 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. Key words Key wordsflow chemistry - photochemistry - trans-cyclooctene - large scale - bioorthogonal Full Text References References 1 Sletten EM. Bertozzi CR. Angew. Chem. Int. Ed. 2009; 48: 6974 2 Patterson DM. Nazarova LA. Prescher JA. ACS Chem. Biol. 2014; 9: 592 3 Lang K. Chin JW. ACS Chem. Biol. 2014; 9: 16 4 McKay CS. Finn MG. Chem. Biol. 2014; 21: 1075 5 Ramil CP. Lin Q. Chem. Commun. 2013; 11007 6 MacKenzie DA. Sherratt AR. Chigrinova M. Cheung LL. W. 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