On-DNA Cross-Dehydrogenative Coupling Reaction toward the Synthesis of Focused DNA-Encoded Tetrahydroisoquinoline Libraries

To expand the chemical space of DNA-encoded library (DEL) technology, we have developed the DNA-compatible cross-dehydrogenative coupling reaction between tetrahydroisoquinolines (THIQs) and a series of nucleophiles such as nitromethane, terminal alkynes, and so on. Both photo- and metal-promoted co...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 15; pp. 5721 - 5725
Main Authors Wen, Xin, Duan, Zhiqiang, Liu, Jiaxiang, Lu, Weiwei, Lu, Xiaojie
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.08.2020
Subjects
alkynes
Lewis bases
tetrahydroisoquinolines
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Summary:To expand the chemical space of DNA-encoded library (DEL) technology, we have developed the DNA-compatible cross-dehydrogenative coupling reaction between tetrahydroisoquinolines (THIQs) and a series of nucleophiles such as nitromethane, terminal alkynes, and so on. Both photo- and metal-promoted conditions have been successfully established for this C-1 derivation of THIQs, as exemplified by the addition of nitromethane. All of these new DNA-compatible transformations have paved the way for the divergent oriented synthesis of THIQ-focused DELs.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c01565