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. Author manuscript; available in PMC: 2009 Nov 1.
Published in final edited form as: J Comb Chem. 2008 Oct 21;10(6):941–947. doi: 10.1021/cc800120y

Scheme 4.

Scheme 4

Synthesis of Benzo[b]furans 14 using Various Palladium-Catalyzed Reactions

Method A (Suzuki-Miyaura coupling): 10% Pd(PPh3)4, KOH (3.0 equiv), 10 (1.5 equiv), toluene/EtOH/H2O (20/5/1), reflux; Method B (carbonylative Suzuki coupling): CO (1 atm), 3 mol % PdCl2(PPh3)2, K2CO3 (3.0 equiv), NaI (3.0 equiv), 10 (1.1 equiv), anisole, 80 °C; Method C (Sonogashira coupling): 3% PdCl2(PPh3)2, 3% CuI, Et2NH, 6 (1.2 equiv), DMF, 50 °C; Method D (Heck coupling): 5 mol % Pd(OAc)2, n-Bu4NI (1.0 equiv), Na2CO3 (2.5 equiv), R3CH=CH2 12 (1.2 equiv), DMF, 80 °C; Method E (carboalkoxylation): CO (1 atm), 3 mol % Pd(OAc)2, 5 mol % dppf, TEA (2.0 equiv), R3OH 13 (1.5 equiv), DMF, 70 °C.