Huang Chunhui, Gevorgyan Vladimir
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
J Am Chem Soc. 2009 Aug 12;131(31):10844-5. doi: 10.1021/ja904791y.
It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.
结果表明，叔丁基二苯基硅基（TBDPS）保护基团可通过钯催化的C-H芳基化反应，作为邻溴苯酚的有效苯基供体，随后对所得硅环进行常规的四丁基氟化铵（TBAF）脱保护。按相同顺序使用新设计的Br-TBDPS保护基团，可在苯酚和苯胺的邻位轻松引入苯基。或者，在最后一步将脱硅反应切换为氧化反应，可将形成的硅环转化为有价值的邻联苯酚。
