874895-85-9Relevant articles and documents
Remote C-H bond functionalization reveals the distance-dependent isotope effect
Li, Jiao-Jie,Giri, Ramesh,Yu, Jin-Quan
, p. 6979 - 6987 (2008/09/21)
Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage.
Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter
Chen, Xiao,Li, Jiao-Jie,Hao, Xue-Shi,Goodhue, Charles E.,Yu, Jin-Quan
, p. 78 - 79 (2007/10/03)
The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C-H bonds with organometallic reagents. A variety of tetraalkyltins were coupled to C-H bonds to give the alkylated products in good yields by using 5 mol % Pd(OAc)2 as the catalyst. Benzoquinone was shown to be essential for the C-H activation when substrates containing non-π-conjugated chelating groups are used. Monitoring the formation and reductive elimination of the Pd(Ar)(Me)L2 complex also revealed that benzoquinone promotes the reductive elimination step. Microwave irradiation enhances the reaction rate drastically. The versatility of this protocol was demonstrated by using substrates containing either oxazoline or pyridine as directing groups. Copyright
