81940-40-1Relevant academic research and scientific papers
Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction
M?kosza, Mieczys?aw,Bechcicka, Ma?gorzata,Wojciechowski, Krzysztof
, p. 175 - 181 (2020/09/21)
Acetals of dimethyl phenyl- and heteroaryl-α-hydroxymethanephosphonates were deprotonated to generate carbanions, which enter the vicarious nucleophilic substitution (VNS) of hydrogen in aromatic nitro compounds to form 4-nitrobenzhydrylphosphonates and α
Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: Synthetic ambit and DFT reactivity predictions
Lovato, Kaitlyn,Guo, Lirong,Xu, Qing-Long,Liu, Fengting,Yousufuddin, Muhammed,Ess, Daniel H.,Kürti, László,Gao, Hongyin
, p. 7992 - 7999 (2018/11/03)
A transition metal-free dehydrogenative method for the direct mono-arylation of a wide range of activated C(sp3)-H bonds has been developed. This operationally simple and environmentally friendly aerobic arylation uses tert-BuOK as the base and nitroarenes as electrophiles to prepare up to gram quantities of structurally diverse sets (>60 examples) of α-arylated esters, amides, nitriles, sulfones and triaryl methanes. DFT calculations provided a predictive model, which states that substrates containing a C(sp3)-H bond with a sufficiently low pKa value should readily undergo arylation. The DFT prediction was confirmed through experimental testing of nearly a dozen substrates containing activated C(sp3)-H bonds. This arylation method was also used in a one-pot protocol to synthesize over twenty compounds containing all-carbon quaternary centers.
Nucleophilic substitution reactions of benzyl- and diphenylmethylphosphonamidic chlorides with amines: Competition between the usual SN2(P) mechanism and elimination-addition with an alkylideneoxophosphorane (phosphene) intermediate
Harger, Martin J. P.
, p. 41 - 47 (2007/10/03)
The substitution reaction of PhCH2P(O)(NMe2)Cl with Me2NH or Et2NH in CHCI3 is very sensitive to the bulk of the nucleophile (≥ 200 times slower with Et2NH), affords only the product derive
