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Phosphine‐Free Stille–Migita Chemistry for the Mild and Orthogonal Modification of DNA and RNA
Author(s) -
Krause André,
Hertl Alexander,
Muttach Fabian,
Jäschke Andres
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404843
Subject(s) - oligonucleotide , stille reaction , nucleic acid , chemistry , combinatorial chemistry , phosphine , nucleoside , monomer , dna , rna , catalysis , nucleotide , organic chemistry , biochemistry , polymer , gene
An optimized catalyst system of [Pd 2 (dba) 3 ] and AsPh 3 efficiently catalyzes the Stille reaction between a diverse set of functionalized stannanes and halogenated mono‐, di‐ and oligonucleotides. The methodology allows for the facile conjugation of short and long nucleic acid molecules with moieties that are not compatible with conventional chemical or enzymatic synthesis, among them acid‐, base‐, or fluoride‐labile protecting groups, fluorogenic and synthetically challenging moieties with good to near‐quantitative yields. Notably, even azides can be directly introduced into oligonucleotides and (deoxy)nucleoside triphosphates, thereby giving direct access to “clickable” nucleic acids.