scholarly journals Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines

2015 ◽  
Vol 11 ◽  
pp. 1933-1943 ◽  
Author(s):  
Ya Lin Tnay ◽  
Gim Yean Ang ◽  
Shunsuke Chiba
Keyword(s):  
Bond Cleavage ◽  
Grignard Reagents ◽  
Radical Intermediate ◽  
Reaction Conditions ◽  
Radical Process ◽  
Radical Fragmentation ◽  
Aerobic Reaction

We report herein studies on copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.

ChemInform Abstract: Fe-Promoted Cross Coupling of Homobenzylic Methyl Ethers with Grignard Reagents via sp3C-O Bond Cleavage.

ChemInform ◽  
2013 ◽  
Vol 44 (52) ◽  
pp. no-no
Author(s):  
Shuang Luo ◽  
Da-Gang Yu ◽  
Ru-Yi Zhu ◽  
Xin Wang ◽  
Lei Wang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Grignard Reagents

ChemInform Abstract: Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage.

ChemInform ◽  
2016 ◽  
Vol 47 (4) ◽  
pp. no-no
Author(s):  
Mamoru Tobisu ◽  
Tsuyoshi Takahira ◽  
Naoto Chatani
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Grignard Reagents

scholarly journals Light-Driven Depolymerization of Native Lignin Enabled by Proton- Coupled Electron Transfer

2019 ◽  
Author(s):  
Suong Nguyen ◽  
Phillip Murray ◽  
Robert Knowles
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Bond Cleavage ◽  
Direct Conversion ◽  
Alkoxy Radical ◽  
Radical Intermediate ◽  
Polymer Backbone ◽  
Good Efficiency ◽  
Chemical Reagents ◽  
Proton Coupled Electron Transfer

<div><p>Here we report a catalytic, light-driven method for the redox-neutral depolymerization of native lignin biomass at ambient temperature. This transformation proceeds via a proton-coupled electron-transfer (PCET) activation of an alcohol O–H bond to generate a key alkoxy radical intermediate, which then drives the <i>β</i>-scission of a vicinal C–C bond. Notably, this depolymerization is driven solely by visible light irradiation, requiring no stoichiometric chemical reagents and producing no stoichiometric waste. This method exhibits good efficiency and excellent selectivity for the activation and fragmentation of <i>β</i>-O-4 linkages in the polymer backbone, even in the presence of numerous other PCET-active functional groups. DFT analysis suggests that the key C–C bond cleavage reactions produce non-equilibrium product distributions, driven by excited-state redox events. These results provide further evidence that visible-light photocatalysis can serve as a viable method for the direct conversion of lignin biomass into valuable arene feedstocks.</p></div>

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)–N Bond Cleavage under Catalyst-Free Conditions

2019 ◽  
Vol 84 (18) ◽  
pp. 11823-11838 ◽  
Author(s):  
Popuri Sureshbabu ◽  
Sadaf Azeez ◽  
Nalluchamy Muniyappan ◽  
Shahulhameed Sabiah ◽  
Jeyakumar Kandasamy
Keyword(s):  
Bond Cleavage ◽  
Grignard Reagents ◽  
Catalyst Free ◽  
Chemoselective Synthesis ◽  
Aryl Ketones

scholarly journals Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transfer Reaction ◽  
Bond Cleavage ◽  
Electron Transfer Reaction ◽  
Amide Bond ◽  
Single Electron Transfer ◽  
Reaction Conditions ◽  
Metal Free ◽  
Single Electron Transfer Reaction

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF3 Bond Cleavage

2019 ◽  
Vol 84 (9) ◽  
pp. 5635-5644 ◽  
Author(s):  
Longzhi Zhu ◽  
Liyuan Le ◽  
Mingpan Yan ◽  
Chak-Tong Au ◽  
Renhua Qiu ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Brønsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3609-3618 ◽  
Author(s):  
Yanzhong Li ◽  
Yulei Zhao ◽  
Yang Yuan ◽  
Lingkai Kong ◽  
Fangfang Zhang
Keyword(s):  
Reaction Mechanism ◽  
Bond Cleavage ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
Esi Ms ◽  
Ms Analysis ◽  
Brönsted Acid

A novel gold(I)/Brønsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Brønsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp2)-H functionalization of enaminones and Brønsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.

Zur Reaktion von 1-Sila-2,4-cyclohexadien mit tert-Butyllithium/Trimethylchlorsilan / On the Reaction of 1-Sila-2,4-cyclohexadiene with tert-Butyllithium/Trimethylchlorosilane

1984 ◽  
Vol 39 (10) ◽  
pp. 1368-1374 ◽  
Author(s):  
Peter Jutzi ◽  
Gabriele Berg ◽  
Cornelius Otto ◽  
Thomas Wippermann
Keyword(s):  
Nucleophilic Substitution ◽  
Bond Cleavage ◽  
Lithium Hydride ◽  
Pure Form ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Nmr Data ◽  
Silicon Carbon ◽  
System 1 ◽  
C Nmr

In the system 1-sila-2,4-cyclohexadiene (l)/tert-butyllithium/trimethylchlorosilane the following reaction types have been observed: nucleophilic substitution, metallation, addition of tert-butyllithium to the diene fragment, addition of lithium hydride to the diene fragment, silicon-carbon bond cleavage, and transmetallation. The resulting products 2-11 have been characterised by their 1H and 13C NMR data; the compounds 2, 3, 6, 8 and 10 could be isolated in a pure form. The relative quantities obtained of the compounds 2-11 depend on the reaction conditions (solvent, temperature, order of addition).

scholarly journals Intramolecular C–F and C–H bond cleavage promoted by butadienyl heavy Grignard reagents

2014 ◽  
Vol 5 (1) ◽  
Author(s):  
Heng Li ◽  
Xiao-Ye Wang ◽  
Baosheng Wei ◽  
Ling Xu ◽  
Wen-Xiong Zhang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Grignard Reagents

ChemInform Abstract: Iron-Promoted C-C Bond Cleavage of 1,3-Diketones: A Route to 1,2-Diketones under Mild Reaction Conditions.

ChemInform ◽  
2011 ◽  
Vol 42 (48) ◽  
pp. no-no
Author(s):  
Lehao Huang ◽  
Kai Cheng ◽  
Bengben Yao ◽  
Yongju Xie ◽  
Yuhong Zhang
Keyword(s):  
Bond Cleavage ◽  
Reaction Conditions
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