1610460-77-9Relevant academic research and scientific papers
Palladium-Catalyzed Chemoselective Activation of sp3 vs sp2 C-H Bonds: Oxidative Coupling to Form Quaternary Centers
Hong, Gang,Nahide, Pradip D.,Neelam, Uday Kumar,Amadeo, Peter,Vijeta, Arjun,Curto, John M.,Hendrick, Charles E.,Vangelder, Kelsey F.,Kozlowski, Marisa C.
, p. 3716 - 3724 (2019/04/13)
The oxidative activation of alkyl C-H bonds vs arene C-H bonds with Pd(OAc)2 has been found to be generalizable to a number of nucleophilic substrates, allowing the formation of a range of hindered quaternary centers. The substrates share a common mechanistic path wherein Pd(II) initiates an oxidative dimerization. The resultant dimer modifies the palladium catalyst to favor activation of alkyl C-H bonds, in contrast to the trends typically observed via a concerted metalation-deprotonation mechanism. Notably, insertion occurs at the terminus of the alkyl arene for hindered substrates. Two different oxidant systems were discovered that turn over the process. Parameters have been identified that predict which substrates are productive in this reaction.
Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones
Susanti, Dewi,Ng, Linda Li Ru,Chan, Philip Wai Hong
, p. 353 - 358 (2014/05/20)
2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)- mediated 1,2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel in n-hexane/ ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.
