Concepedia

Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2‘-Deoxynucleosides and Nucleosides

Jiangqiong Liu, Morris J. Robins

Organic Letters · 2005 · 88 citations · 18 references

DOI

Concepts

Abstract

[reaction: see text] Protected 2'-deoxynucleoside and nucleoside derivatives of 6-fluoropurine, 6-(3-methylbutyl)sulfanylpurine, and 6-(3-methylbutyl)ylsulfonylpurine undergo nickel- or palladium-mediated C-C cross-coupling with arylboronic acids to give good yields of 6-arylpurine products.

References

18

Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides:  Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids

Michal Hocek, Ivan Votruba, Hana Dvořáková · Journal of Medicinal Chemistry · 2000 · 204 citations

, , +8

Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes

Srinivas Reddy Dubbaka, Pierre Vogel · Journal of the American Chemical Society · 2003 · 163 citations · Full text

, , +16

Palladium-Catalyzed Suzuki−Miyaura Cross-Couplings of Sulfonyl Chlorides and Boronic Acids

Srinivas Reddy Dubbaka, Pierre Vogel · Organic Letters · 2003 · 156 citations · Full text

, , +9

Nickel-Assisted Carbon-Fluorine Bond Activation of 2,4,6-Trifluoropyrimidine: Synthesis of New Pyrimidine and Pyrimidinone Derivatives

Thomas Braun, S.P. Foxon, Robin N. Perutz et al. · Angewandte Chemie International Edition · 1999 · 122 citations

, , +8

Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides

Michal Hocek, Ivan Votruba, Hana Dvořáková · Collection of Czechoslovak Chemical Communications · 2001 · 105 citations

, , +12