MC White/Q Chen Chem 153 Cross-Coupling- 122 Week of october 8, 2002 Sonogashira: FG Tolerance pd(CHaCN)cl(4 mol%) PMBO OH CO,Me Cul(14%), Et3N(5 eq) CO,Me CH3CN,-20° C to rt reduc oxidative addition Mec Meo Cul OrMe Meo,c OMe OMe n azole c Hillier, M.C. Meyers, A L JOC 2001, 66, 6037-6045M.C White/Q. Chen Chem 153 Cross-Coupling-122- Week of October 8, 2002 Sonogashira: FG Tolerance PMBO OH H O N CO2Me MeO I O N MeO2C MeO Pd I L L PMBO OH CuI L Pd L PMBO OH O N CO2Me MeO PMBO OH O N CO2Me MeO + Pd(CH3CN)2Cl2 (4 mol%), CuI (14%), Et3N (5 eq) CH3CN, -20 °C to rt 87% L = CH3CN in situ deprotonation oxidative addition transmetalation reductive elimination O OMe N O O N OMe O O O Disorazole C1 Functional groups well tolerated: ester, free hydroxyl, allylic ether, and benzylic ethers, etc. Hillier, M.C.; Meyers, A.I. JOC 2001, 66, 6037-6045