Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 10, Pages 2960-2965Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304120
Keywords
aryldiazonium salts; cross-coupling; green chemistry; N-heteroarenes; photoredox catalysis; water
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Funding
- National Natural Science Foundation of China [21372148]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT 1070]
- Shaanxi Innovative Team of Key Science and Technology [2013KCT-17]
- EPSRC [EP/K039687/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K039687/1] Funding Source: researchfish
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A highly effective visible light-promoted radical-type coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)(3)]Cl(2)6H(2)O as a photosensitizer and a commercial household light bulb as a light source. Pyridine and a variety of substituted pyridines are effective substrates under these reaction conditions, and only monosubstituted products are formed with different regioselectivities. Using aqueous formic acid as solvent, an array of xanthenes, thiazole, pyrazine, and pyridazine are compatible with this new arylation approach. The broad substrate scope, mild reaction conditions, and use of water as reaction solvent make this procedure a practical and environmentally friendly method for the synthesis of compounds containing aryl-heteroaryl motifs.
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