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. 2022 Sep 27;13(39):9156–9164. doi: 10.1021/acs.jpclett.2c01851

Scheme 1. Synthesis of the Model Compounds 1–3 a-b.

Scheme 1

Reagents and Conditions: a) Xantphos, Pd2(dba)3, NEt3, KSCOCH3, toluene, 100 °C, 15 h, 57%; b) Xantphos, Pd2(dba)3, NEt3, NaSCH3, toluene, 100 °C, 18 h, 62%; c) NaNO2, KI, p-TsOH, CH3CN, 0 °C – rt., 65%; d) 1.) KOH, CH3OH, rt., 2 h, 2.) CH3I, 2 h, rt., quant.; e) 1.) KOH, CH3OH, rt., 2 h, 2.) AlCl3, ClC(CH3)3, 4 h, rt., 86%; f) K2CO3, CH3I, DMF, 45 °C, 24 h, 86%; g) Cs2CO3, NaSCH3, DMAc, 110 °C, 16 h, 73%; h) Cs2CO3, KSC(CH3)3, DMAc, 110 °C, 32 h, 44%; i) CuI, Pd(PPh3)2Cl2, THF, NEt3, 14-17 h; j) K2CO3, CuI, Pd(PPh3)4, THF, CH3OH, NEt3, 16 h; k) Bi(OTf)3, ClCOCH3, CH2Cl2, 38%; l) BBr3, ClCOCH3, CH2Cl2, 51%.