Metal-Free C=C Double Bond Cleavage on Enaminones for the Synthesis of α-Ketoamides by Free-Radical Aerobic Oxygenation

2019 ◽  
Vol 2019 (27) ◽  
pp. 4422-4425 ◽  
Author(s):  
Yiming Yang ◽  
Guofeng Zhong ◽  
Junfen Fan ◽  
Yunyun Liu
Keyword(s):  
Free Radical ◽  
Double Bond ◽  
Bond Cleavage ◽  
Metal Free

Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage

Synlett ◽  
2020 ◽  
Author(s):  
Qingle Zeng ◽  
Jie Feng ◽  
Qiaoling Zhang ◽  
Fuhai Li ◽  
Lu Yang ◽  
...  
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Phosphine Oxides ◽  
One Pot ◽  
Metal Free ◽  
Cross Coupling Reaction

AbstractA transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

ChemInform Abstract: Metal Free Access to Amide Compounds via Peroxide-Mediated N=N Double Bond Cleavage of Azobenzenes.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Gang Hong ◽  
Dan Mao ◽  
Xiaoyan Zhu ◽  
Shengying Wu ◽  
Limin Wang
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Free Access ◽  
Metal Free

Metal free access to amide compounds via peroxide-mediated NN double bond cleavage of azobenzenes

2015 ◽  
Vol 2 (8) ◽  
pp. 985-989 ◽  
Author(s):  
Gang Hong ◽  
Dan Mao ◽  
Xiaoyan Zhu ◽  
Shengying Wu ◽  
Limin Wang
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Free Access ◽  
Metal Free ◽  
Direct Amidation

A direct amidation of aldehydes or benzylamines with azobenzenes through TBHP-mediated NN double bond cleavage of azobenzenes has been developed.

Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert-Butyl Hydroperoxide

Synlett ◽  
2017 ◽  
Vol 28 (12) ◽  
pp. 1481-1485 ◽  
Author(s):  
Mehdi Adib ◽  
Rahim Pashazadeh ◽  
Seyed Gohari ◽  
Fatemeh Shahsavari
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
New Strategy

A novel tert-butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.

Ambient and aerobic carbon–carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

2019 ◽  
Vol 21 (12) ◽  
pp. 3436-3441 ◽  
Author(s):  
Qing Yu ◽  
Yating Zhang ◽  
Jie-Ping Wan
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
Rose Bengal ◽  
Bond Cleavage ◽  
Product Diversity ◽  
Carbon Bond ◽  
Metal Free ◽  
Carbon Carbon Bond ◽  
Green Led ◽  
Led Irradiation

With a low loading of Rose Bengal (1 mol%) and green LED irradiation, α-ketoesters are efficiently synthesized with excellent product diversity and selectivity via the ambient cleavage of the enaminone CC double bond.

Deaminative carbonylative thioesterification of activated alkylamines with thiophenols under transition-metal-free conditions

2021 ◽  
Author(s):  
Fengqian Zhao ◽  
Xiao-Feng Wu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

A transition-metal-free radical carbonylation of activated alkylamines with thiophenols has been successfully developed. Various thioesters were selectively produced with moderate to good yields.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

Metal-Free Cascade Methylation/Cyclization of N-Alkyl-N-methacryloylbenzamides with Dicumyl Peroxide

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 617-620 ◽  
Author(s):  
Yan-Ning Niu ◽  
Xiao-Feng Xia ◽  
Yuan Yuan
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Metal Free ◽  
Wide Range ◽  
Radical Cascade ◽  
Convenient Access

A metal-free radical cascade methylation/cyclization of a wide range of N-alkyl-N-methacryloylbenzamides by using dicumyl peroxide as the methylating reagent provides a convenient access to a series of methylated isoquinoline-1,3-diones in moderate yields.

Unusual carboncarbon double bond cleavage in thiophenohomotropone system promoted by ethanedithiol

1982 ◽  
Vol 23 (28) ◽  
pp. 2859-2862 ◽  
Author(s):  
Bernard Hanquet ◽  
Mohammed El Borai ◽  
Roger Guilard ◽  
Yves Dusausoy
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Carbon Double Bond
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