Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 19, Pages 3678-3683Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000313
Keywords
Nucleosides; Cross-coupling; Palladium; Nitrogen heterocycles
Categories
Funding
- National Science Foundation (NSF) [CHE-0124255]
- University of Alabama
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A variety of applications of C-alkynylated nucleosides has prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient and environmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueous solvent. The combination of Pd(OAc)(2), CuI, and TXPTS [trisodium tri(2,4-dimethy1-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromopurines and 5-iodouridine in H2O/CH3CN (1:1) in yields ranging from 42 to 98%.
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