Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel‐catalyzed C−N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic...

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Veröffentlicht in:Angewandte Chemie International Edition 2018-03, Vol.57 (13), p.3488-3492
Hauptverfasser: Kim, Taehoon, McCarver, Stefan J., Lee, Chulbom, MacMillan, David W. C.
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Sprache:eng
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Zusammenfassung:Herein we report a highly efficient method for nickel‐catalyzed C−N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy‐transfer mechanism wherein C−N bond reductive elimination occurs from a triplet excited NiII complex. Late‐stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated. A method for C−N bond formation between sulfonamides and aryl electrophiles is reported. This method provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy‐transfer mechanism wherein C−N bond reductive elimination occurs from a triplet excited NiII complex.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201800699