22693-41-0Relevant academic research and scientific papers
Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination
Ganley, Jacob M.,Knowles, Robert R.,Nocera, Daniel G.,Qin, Yangzhong,Sun, Rui,Zhu, Qilei
supporting information, p. 10232 - 10242 (2021/07/26)
The reaction mechanism and the origin of the selectivity for the photocatalytic intermolecular anti-Markovnikov hydroamination of unactivated alkenes with primary amines to furnish secondary amines have been revealed by time-resolved laser kinetics measur
Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
Miller, David C.,Ganley, Jacob M.,Musacchio, Andrew J.,Sherwood, Trevor C.,Ewing, William R.,Knowles, Robert R.
supporting information, p. 16590 - 16594 (2019/11/03)
We report here a photocatalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for secondary over tertiary amine products, even though the secondary amines are established substrates for ARC-based olefin amination under similar conditions.
Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer
Zhu, Qilei,Graff, David E.,Knowles, Robert R.
supporting information, p. 741 - 747 (2018/01/26)
Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiol hydrogen atom donor. Reaction outcomes are consistent with the intermediacy of an N-centered sulfonamidyl radical generated via proton-coupled electron transfer activation of the sulfonamide N-H bond. Studies outlining the synthetic scope (>60 examples) and mechanistic features of the reaction are presented.
Phosphine/Lewis acid mediated Reformatsky-type reaction of α-bromoketone or -thioester derivatives
Hashimoto, Yukihiko,Kikuchi, Satoshi
, p. 126 - 127 (2007/10/03)
The combination of (?-tolyl)3P/TiCl4 effectively promoted the Reformatsky-type reaction of α-bromoketone or -thioester derivatives with various aldehydes, and the corresponding β-hydroxy carbonyl compounds were obtained in good yield
A convergent asymmetric synthesis of γ-butenolides
Renard, Marc,Ghosez, Léon A.
, p. 2597 - 2608 (2007/10/03)
The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of γ-butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin.
Formation by SRN1 reactions and 1H N.M.R. properties of sterically encumbered 2,4,6-triaIkyIphenyl p-nitrobenzyl sulfides
Look, Kai,Norris, Robert K.
, p. 1077 - 1083 (2007/10/03)
Sterically hindered p-nitrobenzylic chlorides (1) and (2) react with the sodium salts of 2,4,6-trialkylbenzenethiols (3a)-(5a) by the SRN1 reaction to give good yields of the corresponding p-nitrobenzylic aryl sulfides (6)-(10). For example, th
A convergent asymmetric synthesis of γ-butenolides
Renard, Marc,Ghosez, Leon
, p. 6237 - 6240 (2007/10/03)
Addition of aldehydes to the new enantiomerically pure lithiated sulfoxide 4 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The reaction with ketones was less stereoselective.
Novel synthetic pathways to neutral mixed-ligand iron-sulfur clusters
Harmjanz,Junghans,Opitz,Bahlmann,Pohl
, p. 1040 - 1048 (2007/10/03)
The reaction of [Fe(N(SiMe3)2)2] with thiols RSH, elemental sulfur, and neutral ligands L (with sulfur donor atoms, e.g. thiourea derivatives) gives [Fe4S4(SR)2L2] clusters in hi
The Preparation, Structure, and Reactions of the Mononuclear Thiolate-Hydride Complexes (R = Bulky Alkyl or Aryl Group, dppe = Ph2PCH2CH2PPh2); X-Ray Structure Determination of cis-i3-2,4,6)(dppe)2>
Henderson, Richard A.,Hughes, David L.,Richards, Raymond L.,Shortman, Caroline
, p. 1115 - 1122 (2007/10/02)
Reaction of trans- (dppe = Ph2PCH2CH2PPh2) with the bulky thiols RSH (R = Pri, But, C6H2Me3-2,4,6, C6H2Pri3-2,4,6 or C6H2BrPri2-4,2,6) at reflux in tetrahydrofuran (thf) gives the green hydride complexes .The complex cis-i3-2,4,6)(dppe)2>.0.5C6H5Me has a distorted octahedral structure, with distances: Mo-S 2.402(2), Mo-H 1.61(9), Mo-P 2.380(2)-2.465(2) Angstroem.The 1H hydride resonances of these compounds occur in the range -3.98 to -4.98 p.p.m. (relative to SiMe4) and show fluxionality at room temperature with respect to the phosphorus atoms except for R = C6H2BrPri2-4,2,6.Other spectroscopic properties of the compounds are used as a basis to discuss the mechanism of their formation.The complex i3-2,4,6-)(dppe)2> reacts at 20 deg C with CO or ButNC to give the known compounds and tNC)2(dppe)2>, and with PhSH to give trans-.
Rhenium Nitrosyl Complexes with Simple and with Sterically Demanding Aromatic Thiolate Ligands: X-Ray Crystal Structures of *CH2Cl2 and i2-2,6)4(NO)>
Blower, Philip J.,Dilworth, Jonathan R.,Hutchinson, John P.,Zubieta, Jon A.
, p. 1533 - 1542 (2007/10/02)
Reaction of with a range of thiophenols under basic conditions gives one of two classes of products depending on the steric requirements of the thiols.A representative member of each class has been characterised by an X-ray crystal
