scholarly journals Transition-Metal-Free Radical C(sp3)–C(sp2) and C(sp3)–C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners

2017 ◽  
Vol 139 (45) ◽  
pp. 16327-16333 ◽  
Author(s):  
Minyan Li ◽  
Simon Berritt ◽  
Lucas Matuszewski ◽  
Guogang Deng ◽  
Ana Pascual-Escudero ◽  
...  
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Electron Donors ◽  
Metal Free

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...

scholarly journals SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Dong Zou ◽  
Lishe Gan ◽  
Fan Yang ◽  
Huan Wang ◽  
Youge Pu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Experimental Evidence ◽  
Radical Anion ◽  
Reaction Pathway ◽  
Cycloaddition Reaction ◽  
Electron Donors ◽  
Ring Closure ◽  
Computational Studies ◽  
Metal Free ◽  
Radical Coupling

AbstractThe use of nitroarenes as amino sources in synthesis is challenging. Herein is reported an unusual, straightforward, and transition metal-free method for the net [3 + 2]-cycloaddition reaction of 2-azaallyl anions with nitroarenes. The products of this reaction are diverse 2,5-dihydro-1,2,4-oxadiazoles (>40 examples, up to 95% yield). This method does not require an external reductant to reduce nitroarenes, nor does it employ nitrosoarenes, which are often used in N–O cycloadditions. Instead, it is proposed that the 2-azaallyl anions, which behave as super electron donors (SEDs), deliver an electron to the nitroarene to generate a nitroarene radical anion. A downstream 2-azaallyl radical coupling with a newly formed nitrosoarene is followed by ring closure to afford the observed products. This proposed reaction pathway is supported by computational studies and experimental evidence. Overall, this method uses readily available materials, is green, and exhibits a broad scope.

Transition-metal-free polycyclic indoline formation via a free radical pathway: a computational mechanistic study

2020 ◽  
Vol 139 (3) ◽  
Author(s):  
Chenguang Luo ◽  
Lin Lu ◽  
Lin Zhang ◽  
Zuoyin Yang ◽  
Min Pu ◽  
...  
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Mechanistic Study ◽  
Metal Free

scholarly journals α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

2017 ◽  
Vol 8 (10) ◽  
pp. 6888-6892 ◽  
Author(s):  
Xinjun Tang ◽  
Armido Studer
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented.

scholarly journals Organic super-electron-donors: initiators in transition metal-free haloarene–arene coupling

2014 ◽  
Vol 5 (2) ◽  
pp. 476-482 ◽  
Author(s):  
Shengze Zhou ◽  
Greg M. Anderson ◽  
Bhaskar Mondal ◽  
Eswararao Doni ◽  
Vicki Ironmonger ◽  
...  
Keyword(s):  
Transition Metal ◽  
Electron Donors ◽  
Metal Free

Transition-metal-free radical fluoroalkylation of isocyanides for the synthesis of tri-/di-/monofluoromethylated phenanthridines

2017 ◽  
Vol 4 (10) ◽  
pp. 2049-2053 ◽  
Author(s):  
Jing Fang ◽  
Wei-Guo Shen ◽  
Gui-Zhen Ao ◽  
Feng Liu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

A convenient and scalable protocol is developed for the radical fluoroalkylation of 2-isocyanobiphenyls under transition-metal-free conditions.

Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes

2018 ◽  
Vol 2019 (2-3) ◽  
pp. 309-312
Author(s):  
Kiran Matcha ◽  
Andrey P. Antonchick
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

scholarly journals Transition-metal-free C(sp3)–H/C(sp3)–H dehydrogenative coupling of saturated heterocycles with N-benzyl imines

2020 ◽  
Vol 11 (29) ◽  
pp. 7619-7625 ◽  
Author(s):  
Zhengfen Liu ◽  
Minyan Li ◽  
Guogang Deng ◽  
Wanshi Wei ◽  
Ping Feng ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Transition Metal ◽  
Electron Donors ◽  
Metal Free ◽  
Aryl Radicals ◽  
Dehydrogenative Coupling ◽  
Saturated Heterocycles

A unique transition-metal-free C(sp3)–H/C(sp3)–H dehydrocoupling of N-benzylimines with saturated heterocycles is presented using 2-azaallyl anions as super electron donors to initiate the generation of hydrogen atom abstracting aryl radicals.

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