123296-19-5Relevant academic research and scientific papers
Amidyl Radical Directed Remote Allylation of Unactivated sp3 C?H Bonds by Organic Photoredox Catalysis
Wu, Kui,Wang, Lushun,Colón-Rodríguez, Sonivette,Flechsig, Gerd-Uwe,Wang, Ting
, p. 1774 - 1778 (2019)
The development of visible-light-mediated allylation of unactivated sp3 C?H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre-functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C?H allylation products in good yields. A variety of electron deficient allyl sulfone systems could be used as δ-carbon radical acceptor.
Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
Lee, Melissa,Sanford, Melanie S.
supporting information, p. 572 - 575 (2017/02/10)
This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
Metal-free oxidative functionalization of C(sp3)-H bond adjacent to oxygen and radical addition to olefins
Zhou, Wei,Qian, Ping,Zhao, Jincan,Fang, Hong,Han, Jianlin,Pan, Yi
supporting information, p. 1160 - 1163 (2015/03/14)
A DTBP-promoted oxidative functionalization of a C(sp3)-H bond adjacent to oxygen and intermolecular radical addition to olefins without use of any metal catalyst or photoredox catalysis is reported. The reaction has a wide scope of olefin, alcohol, and cycloether substrates, which provides an easy way for direct preparation of α,ω-amino alcohols.
N-LITHIO-N-(2-LITHIOETHYL)- AND N-LITHIO-N-(3-LITHIOPROPYL)-BENZAMIDE: DIRECT PREPARATION AND SYNTHETIC APPLICATIONS OF 2-LITHIOETHYL- AND 3-LITHIOPROPYL-AMINE EQUIVALENTS
Barluenga, Jose,Foubelo, Francisco,Fananas, Francisco J.,Yus, Miguel
, p. 2183 - 2192 (2007/10/02)
The successive reaction of 2-chloroethyl and 3-chloropropyl-benzamide with n-butyl-lithium and lithium naphthalenide at temperatures ranging between -78 and -50 deg C leads to N-lithio-N-(2-lithioethyl)- and N-lithio-N-(3-lithiopropyl)benzamide , which by treatment with different electrophiles (H2O, D2O, Me2S2, CO2, PriCHO, PhCHO, Me2CO, Ph2CO, and O2) yields the expected functionalized benzamides .The acidic and basic hydrolysis of compounds (10) and (11) gives different results depending on the structure of the substrate and the reaction conditions.
