A solvent-induced reversal of regioselectivity in the Suzuki coupling of pyrrole esters
Zhang, Y., & Handy, S. T. (2008). A solvent-induced reversal of regioselectivity in the Suzuki coupling of pyrrole esters. Open Organic Chemistry Journal, 2(1), 58-64. DOI: 10.2174/1874095200802010058
During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a reversal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in regioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.