Fig. 4: Further transformations of linchpin selenonium salt.
From: On-DNA C–H functionalization of electron-rich arenes for DNA-encoded libraries
a, Photochemical iodination of selenonium salt: DNA conjugate (0.3 mM), NaI (1.67 M) in NaPi buffer (0.30 M, pH 6.0), Ar, 25 °C, 450-nm light-emitting diode (LED), 16 h. b, Suzuki cross-coupling: DNA conjugate (0.2 mM), APhos Pd G3 (4 mM), phenylboronic acid or methylboroxine (100 mM) in NaPi buffer (0.25 M, pH 8.0):DMA (3:2), 95 °C, 15 min. c, Pd-mediated hydroxycarbonylation: DNA conjugate (0.17 mM), XantPhos Pd G3 (1.7 mM), trichlorophenyl formate (170 mM) in NaPi buffer (0.17 M, pH 8.0):DMA (1:2), 80 °C, 30 min. d, Pd-mediated cyanation: DNA conjugate (0.2 mM), XantPhos Pd G3 (4 mM), potassium ferrocyanide (80 mM) in NaPi buffer (0.2 M, pH 8.0):NMP (2:1), 95 °C, 15 min. e, Photochemical C–S coupling: DNA conjugate (0.6 mM), 4-methylbenzenethiol (300 mM), K2CO3 (300 mM) in DMSO:water (2:1), Ar, 25 °C, 456-nm LED, 15 min. f, Minisci-type arylation: DNA conjugate (0.3 mM), 1,2,2,6,6-pentamethylpiperidine (16 mM), 3-methylisoquinoline (660 mM) in DMSO:water (9:1), Ar, 25 °C, 450-nm LED, 15 min. Ar, argon; APhos, (4-(N,N-dimethylamino)phenyl)di-tert-butyl phosphine; XantPhos, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene. Depicted DNA fragment: HP–AOP–NH–. See the Methods for more details.
