Visible-Light-Induced C4-Selective Functionalization of Pyridinium Salts with Cyclopropanols
Dr. Mari Vellakkaran
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorTaehwan Kim
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Sungwoo Hong
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
Search for more papers by this authorDr. Mari Vellakkaran
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorTaehwan Kim
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Sungwoo Hong
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS)
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, 34141 Republic of Korea
Search for more papers by this authorDedicated to Professor Jaiwook Park on the occasion of his retirement
Graphical Abstract
Visible-light-induced β-carbonyl alkylation of pyridines was developed by employing various cyclopropanols and N-amidopyridinium salts under mild conditions. This method provides an effective tool for the synthesis of valuable β-pyridyl-functionalized carbonyl frameworks with excellent C4 selectivity and the late-stage functionalization of complex and medicinally relevant molecules.
Abstract
The site-selective C−H functionalization of heteroarenes is of considerable importance for streamlining the rapid modification of bioactive molecules. Herein, we report a general strategy for visible-light-induced β-carbonyl alkylation at the C4 position of pyridines with high site selectivity using various cyclopropanols and N-amidopyridinium salts. In this process, hydrogen-atom transfer between the generated sulfonamidyl radicals and O−H bonds of cyclopropanols generates β-carbonyl radicals, providing efficient access to synthetically valuable β-pyridylated (aryl)ketones, aldehydes, and esters with broad functional-group tolerance. In addition, the mild method serves as an effective tool for the site-selective late-stage functionalization of complex and medicinally relevant molecules.
Conflict of interest
The authors declare no conflict of interest.
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