scholarly journals Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols

2019 ◽  
Author(s):  
John Lopp ◽  
Valerie Schmidt
Keyword(s):  
Functional Groups ◽  
Transfer Process ◽  
Triethyl Phosphite ◽  
Atom Transfer ◽  
Aliphatic Thiols

<div><div><div><p>We report herein the development of an S-atom transfer process using triethyl phosphite as the S-atom acceptor that allows thiols to serve as precursors of C-centered radials. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.</p></div></div></div>

scholarly journals Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols

2019 ◽  
Author(s):  
John Lopp ◽  
Valerie Schmidt
Keyword(s):  
Functional Groups ◽  
Transfer Process ◽  
Triethyl Phosphite ◽  
Atom Transfer ◽  
Aliphatic Thiols

<div><div><div><p>We report herein the development of an S-atom transfer process using triethyl phosphite as the S-atom acceptor that allows thiols to serve as precursors of C-centered radials. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.</p></div></div></div>

Regioselective C(sp3)–H alkylation of a fructopyranose derivative by 1,6-HAT

2021 ◽  
Vol 19 (14) ◽  
pp. 3124-3127
Author(s):  
Yanru Li ◽  
Shoto Miyamoto ◽  
Takeru Torigoe ◽  
Yoichiro Kuninobu
Keyword(s):  
Hydrogen Atom ◽  
Functional Groups ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer

We developed regioselective C(sp3)–H alkylation of a fructopyranose derivative, which enables the introduction of several functional groups, by 1,6-hydrogen atom transfer.

Carbonylative Coupling of Simple Alkanes and Alkenes Enabled by Organic Photoredox Catalysis

2021 ◽  
Author(s):  
Ling Chen ◽  
Jing Hou ◽  
Ming Zheng ◽  
Le-Wu Zhan ◽  
Wan-Ying Tang ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Transfer Process ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Visible Light Driven

A visible-light-driven direct carbonylative coupling of simple alkanes and alkenes via the combination of the hydrogen atom transfer process and photoredox catalysis has been demonstrated. Employing the N-alkoxyazinium salt as...

scholarly journals Experimental and Computational Investigations into Trivalent Phosphorous-Mediated Radical Thiol Desulfurization

2021 ◽  
Author(s):  
John Lopp ◽  
Valerie Schmidt
Keyword(s):  
Atom Transfer ◽  
Radical Intermediate ◽  
Thiyl Radicals ◽  
Trigonal Bipyramidal ◽  
Peptide Modification ◽  
Aliphatic Thiols ◽  
Mechanism And Kinetics ◽  
Kinetics Of ◽  
Marked Dependence ◽  
Distorted Trigonal Bipyramidal

Radical-mediated thiol desulfurization processes using tricoordinate phosphorous reagents are used in a range of applications from small molecule synthesis to peptide modification. A combined experimental and computational examination of the mechanism and kinetics of the radical desulfurization of alkyl thiyl radicals using trivalent phosphorus reagents was performed. Primary alkyl thiols undergo desulfurization between 10^6 to 10^9 M-1s-1 depending on the phosphorus component with either an H-atom transfer step or β-fragmentation of the thiophosphoranyl intermediate may be rate-controlling. While the desulfurization of primary aliphatic thiols showed a marked dependence on the identity of phosphorous reagent used with either a rate-controlling H-atom transfer or -fragmentation, thiols yielding stabilized C-centered radicals showed much less sensitivity. Support for a stepwise S-atom transfer process progressing via a distorted trigonal bipyramidal thiophosphoranyl radical intermediate was obtained from DFT calculated energetics and hyperfine splitting values.

Ion-molecule reactions in acetone-water mixtures

1966 ◽  
Vol 19 (1) ◽  
pp. 59 ◽  
Author(s):  
Souza BC de ◽  
JH Green
Keyword(s):  
Hydrogen Atom ◽  
Proton Transfer ◽  
Transfer Process ◽  
Hydrogen Atom Transfer ◽  
Mass Spectrometric ◽  
Transfer Mechanism ◽  
Atom Transfer ◽  
Ion Molecule Reactions ◽  
Acetone Water

Mass-spectrometric studies of ion-molecule reactions in acetone-water mixtures at 70 eV and 20 eV electron energies are described. The results provide evidence in favour of the proton transfer mechanism rather than for a hydrogen atom transfer process for the production of M + 1 ions.

ChemInform Abstract: Carbon Radical Addition to Glyoxylic Oxime Ether via Iodine Atom-Transfer Process.

ChemInform ◽  
2010 ◽  
Vol 30 (30) ◽  
pp. no-no
Author(s):  
Hideto Miyabe ◽  
Masafumi Ueda ◽  
Naoko Yoshioka ◽  
Takeaki Naito
Keyword(s):  
Transfer Process ◽  
Iodine Atom ◽  
Radical Addition ◽  
Atom Transfer ◽  
Oxime Ether

Carbon Radical Addition to Glyoxylic Oxime Ether via Iodine Atom-Transfer Process

Synlett ◽  
1999 ◽  
Vol 1999 (4) ◽  
pp. 465-467 ◽  
Author(s):  
Hideto Miyabe ◽  
Masafumi Ueda ◽  
Naoko Yoshioka ◽  
Takeaki Naito
Keyword(s):  
Transfer Process ◽  
Iodine Atom ◽  
Radical Addition ◽  
Atom Transfer ◽  
Oxime Ether

scholarly journals K2S2O8-Promoted Aryl Thioamides Synthesis from Aryl Aldehydes Using Thiourea as the Sulfur Source

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2225 ◽  
Author(s):  
Yongjun Bian ◽  
Xingyu Qu ◽  
Yongqiang Chen ◽  
Jun Li ◽  
Leng Liu
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Sulfur Atom ◽  
Coupling Reaction ◽  
Sulfur Source ◽  
Atom Transfer ◽  
Free Condition ◽  
Metal Free ◽  
Aryl Aldehydes ◽  
Three Component Coupling

Thiourea as a sulfur atom transfer reagent was applied for the synthesis of aryl thioamides through a three-component coupling reaction with aryl aldehydes and N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC). The reaction could tolerate various functional groups and gave moderate to good yields of desired products under the transition-metal-free condition.

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