Fig. 2: Substrate scope of NHPI esters. | Nature Communications

Fig. 2: Substrate scope of NHPI esters.

From: Late-stage adenine N6-alkylation of nucleos(t)ides and oligonucleotides via photoredox and copper co-catalytic decarboxylative C(sp3)–N coupling

Fig. 2

a2’-deoxyadenosine (1.0 equiv.), NHPI ester (1.2 equiv.), Ru(bpy)3(PF6)2 (1 mol%), Cu(MeCN)4PF6 (50 mol%), and Et3N (2.5 equiv.) in dry DMA (0.05 M) on 0.2 mmol scale; irradiated by 20 W blue LED *2 at r.t. for 20 h; isolated yield. b1.5 equiv. dibutyl phosphate was added; irradiated by 20 W blue LED *2 at r.t. for 12 h. cthe equivalent of NHPI ester is increased to 2.4 equiv. d2’-deoxyadenosine (1.0 equiv.), 2-(4-methoxyphenyl)acetaldehyde (15.0 equiv.), NaBH3CN (6.0 equiv.), and acetic acid (1.0 M), 50 °C, 12 h; LC-yield. eAcetone was used instead of 2-(4-methoxyphenyl)acetaldehyde. fCyclopentanone was used instead of 2-(4-methoxyphenyl)acetaldehyde. Ph phenyl, Boc tert-butyloxy carbon, PyBA 1-pyrenebutyric acid.

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