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Significance Combinatorial synthesis via DNA encoded library (DEL) has evolved as a technology of great importance in drug discovery. However, the idiosyncratic aqueous, dilute, DNA-sensitive parameters and infinitesimal scale of this system present new challenges for traditional organic reactions. A detailed protocol aiding the transition from organic reactions to reactions with DNA-bound molecules was developed using a tactical combination of kinetic analysis and reaction screening. As an example, the venerable Giese addition was applied to forge high-value C−C bonds, including all-carbon quaternary centers, on DNA, representing the first radical-based synthesis in DEL that expands the traditional toolbox beyond pericyclic, carbonyl-based, and two-electron cross-couplings.

Kinetically guided radical-based synthesis of C(sp 3 )−C(sp 3 ) linkages on DNA

Kinetically guided radical-based synthesis of C(sp ³ )−C(sp ³ ) linkages on DNA