Palladium-catalyzed silylation of aryl bromides leading to functionalized aryldimethylsilanols.
[reaction: see text] A mild and general palladium-catalyzed insertion of 1,2-diethoxy-1,1,2,2-tetramethyldisilane into a variety of aryl bromides affords the aryldimethylsilyl ethers in high yields. Hydrolysis of the ethers under pH-optimized conditions results in the exclusive formation of the desired aryldimethylsilanols.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 S. Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Kallemeyn
Jeffrey M
JM
D000478:Alkylation; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008024:Ligands; D008956:Models, Chemical; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis*
D001965:Bromides; D008024:Ligands; D012821:Silanes; C082343:silanol; D010165:Palladium