Fig. 3: Product diversification.
From: Breaking the ‘rule-of-five’ to access bridged bicyclic heteroaromatic bioisosteres
Diversification of products 26 and 61 using a wide variety of conditions. aPd/C, H2. b9-Borabicyclo(3.3.1)nonane (9-BBN), then H2O2, NaOH. cO3, Me2S, then NH2OBn·HCl, NaOAc. dO3, then NaBH4. e4-(Trifluoromethyl)benzenesulfonyl chloride, Et3N, 4-dimethylaminopyridine (DMAP), then NaBH4. fO3, Me2S, then NaH2PO4, 2-methyl-2-butene, NaClO2. gOxalyl chloride, then NH2OH·HCl, K2CO3. hN-hydroxyphthalimide, N,N′-diisopropylcarbodiimide, DMAP, then [Ir(ppy)2(dtbbpy)]PF6, Et3N, 1,4-cyclohexadiene, 456-nm blue LEDs. iIron powder, NH4Cl. jPhenyl isocyanate. kPhenyl isothiocyanate. lp-Toluenesulfonyl chloride, Et3N, DMAP. mN,N-dimethylsulfamoyl chloride, Et3N, DMAP. nDi-tert-butyl dicarbonate, DMAP. op-Toluoyl chloride, Et3N, DMAP. Tol, 4-methylphenyl; Boc, tert-butoxycarbonyl.
