41764-14-1Relevant academic research and scientific papers
Radical Transformation of Aliphatic C-H Bonds to Oxime Ethers via Hydrogen Atom Transfer
Wang, Xinmou,Yu, Mo,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 8353 - 8358 (2021/10/25)
Herein, we describe a strategy for conversion of aliphatic C-H bonds to oxime ethers via hydrogen atom transfer. In this strategy, the decatungstate anion and sulfate radical play complementary roles in the abstraction of hydrogen atoms from primary, secondary, and tertiary C-H bonds of alkanes. The easy accessibility of alkanes and the broad substrate scope, mild conditions, and excellent regioselectivity of these reactions make this strategy applicable for the transformation of raw materials to high-value chemicals.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, p. 7709 - 7714 (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
Visible-Light-Promoted Activation of Unactivated C(sp3)-H Bonds and Their Selective Trifluoromethylthiolation
Mukherjee, Satobhisha,Maji, Biplab,Tlahuext-Aca, Adrian,Glorius, Frank
supporting information, p. 16200 - 16203 (2016/12/27)
Selective functionalization of ubiquitous C(sp3)-H bonds using visible light is a highly challenging yet desirable goal in organic synthesis. The development of such processes relies on both rational design and serendipitous discoveries from innovative tools such as screening technologies. Applying a mechanism-based screening strategy, we herein report photoredox-mediated hydrogen atom transfer catalysis for the selective activation of otherwise unactivated C(sp3)-H bonds, followed by their trifluoromethylthiolation, which has high potential as a late-stage functionalization tool. The generality of this method is exhibited through incorporation of the trifluoromethylthio group in a large number of C(sp3)-H bonds with high selectivity without the need for an excess of valuable substrate.
NEW SYNTHETIC "TRICKS". ONE-POT PREPARATION OF N-SUBSTITUTED PHTHALIMIDES FROM AZIDES AND PHTHALIC ANHYDRIDE
Garcia, Jordi,Vilarrasa, Jaume,Bordas, Xavier,Banaszek, Anna
, p. 639 - 640 (2007/10/02)
N-Substituted phthalimides can be obtained in very good yields, under essentially neutral conditions, by mixing or heating an alkyl (or aryl) azide, triphenylphosohine, and phthalic anhydride in benzene or toluene, in the presence of a catalytic amount of tetrabutylammonium cyanide.Application of the reaction into the domain of carbohydrates is promising.
