Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanols with substituted aryl halides.
[reaction: see text] A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium tert-butoxide as the activator, (2) the use of copper(I) iodide in stoichiometric quantities, and (3) the use of Pd2(dba)3.CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with a variety of aromatic iodides to afford the coupling products in good yield (70-84%).
Denmark
Scott E
SE
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Baird
John D
JD
D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D007211:Indoles; D012821:Silanes; D010165:Palladium