Nucleophilic Substitution of Selenosulfonates with Me3SiCF2Br: Facile and Efficient Access to Bromodifluoromethylated Selenides under Metal-Free Conditions

2021 ◽  
Author(s):  
Yi Fang ◽  
Xin Li ◽  
Chunyi Liu ◽  
Jie Tang ◽  
Zhengping Chen
Keyword(s):  
Nucleophilic Substitution ◽  
Metal Free ◽  
Efficient Access

Metal-free radical cascade dichloromethylation of activated alkenes using CH2Cl2: highly selective activation of the C–H bond

RSC Advances ◽  
2014 ◽  
Vol 4 (110) ◽  
pp. 64855-64859 ◽  
Author(s):  
Yunfei Tian ◽  
Zhong-Quan Liu
Keyword(s):  
Free Radical ◽  
Dicumyl Peroxide ◽  
Cascade Process ◽  
Selective Activation ◽  
Metal Free ◽  
Efficient Access ◽  
Radical Cascade

A dicumyl peroxide-initiated highly selective activation of the (sp3)C–H bond in dichloromethane (DCM, CH2Cl2) has been achieved, which allows efficient access to dichloronated oxindoles via a free-radical cascade process.

DDQ-mediated regioselective C–S bond formation: efficient access to allylic sulfides

2018 ◽  
Vol 5 (21) ◽  
pp. 3158-3162 ◽  
Author(s):  
Chunsheng Li ◽  
Jianxiao Li ◽  
Chaowei Tan ◽  
Wanqing Wu ◽  
Huanfeng Jiang
Keyword(s):  
Bond Formation ◽  
Metal Free ◽  
Efficient Access

A novel metal-free dehydrocoupling approach for constructing allylic sulfides via oxidative allylic C–H functionalization with high atom- and step-economy has been developed.

scholarly journals Direct intramolecular double cross-dehydrogentive-coupling (CDC) cyclization of N-(2-pyridyl)amidines under metal-free conditions

RSC Advances ◽  
2019 ◽  
Vol 9 (72) ◽  
pp. 42172-42182 ◽  
Author(s):  
Fengping Yi ◽  
Chao Fu ◽  
Qihui Sun ◽  
Huazhen Wei ◽  
Genfa Yu ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Metal Free ◽  
Nucleophilic Substitution Reactions ◽  
Mild Conditions ◽  
Double Cross

A metal-free protocol to form 2-iminoimidazo[1,2-a]-pyridines from N-(2-pyridyl)amidines, in which the constructed heterocyclic skeletons are promoted by CBr4via radical or nucleophilic substitution reactions under mild conditions, is demonstrated.

Transition-Metal-Free, Intermolecular Azidoheteroarylation of Alkenes: Efficient Access to β-Azidoalkylated Quinoxalinones and Preliminary Antifungal Evaluation Against Magnaporthe grisea

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2395-2409
Author(s):  
Weiwei Qin ◽  
Zhaodong Li ◽  
Yiming Du ◽  
Yue Chen ◽  
Yun-Lin Liu
Keyword(s):  
Transition Metal ◽  
Magnaporthe Grisea ◽  
Single Step ◽  
Domino Reaction ◽  
Efficient Synthesis ◽  
Metal Free ◽  
Efficient Access ◽  
First Time ◽  
Antibacterial Evaluation ◽  
Addition Pathway

An efficient, PhI(OAc)2-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.

scholarly journals Nucleophilic C–H functionalization of arenes: a new logic of organic synthesis

2017 ◽  
Vol 89 (8) ◽  
pp. 1195-1208 ◽  
Author(s):  
Oleg N. Chupakhin ◽  
Valery N. Charushin
Keyword(s):  
Electron Transfer ◽  
Green Chemistry ◽  
Nucleophilic Substitution ◽  
Organic Synthesis ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Metal Free ◽  
Hydride Ion ◽  
Electrochemical Modeling ◽  
Leaving Groups ◽  
Concept Change

AbstractDirect metal-free C–H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the SNH reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C–H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The SNH reactions, as a part of the general C–H functionalization concept, change the logic of organic synthesis. They open new opportunities, avoiding incorporation of good leaving groups or other auxiliaries in an aromatic ring, as a prefunctionalization step, thus providing a better correspondence to the principles of green chemistry.

Synthesis and characterization of O- and S-bridged perfluoroalkylated metal-free and zinc phthalocyanines

2013 ◽  
Vol 17 (06n07) ◽  
pp. 555-563 ◽  
Author(s):  
İlke Gürol ◽  
Gülay Gümüş ◽  
Emel Musluoğlu ◽  
Yadigar Arslan ◽  
Vefa Ahsen
Keyword(s):  
Nucleophilic Substitution ◽  
Elemental Analysis ◽  
Synthesis And Characterization ◽  
Polar Solvents ◽  
Metal Free ◽  
Zinc Phthalocyanines ◽  
Ft Ir

The synthesis of tetra and octa perfluoroalkyl substituted zinc and metal free phthalocyanines ( ZnPc and H 2 Pc ) are reported. The compounds 1–5 have been prepared by nucleophilic substitution of 4-nitrophthalonitrile with 1H,1H,2H,2H-perfluorooctanethiol, 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol, 1H,1H-perfluorotetradecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol, respectively. The compounds 6–8 have been prepared by the reaction of 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol with 4,5-dichlororphthalonitrile, respectively. The compound 9 with thia-bridge has been synthesized from 4,5-dichlororphthalonitrile. Zinc and metal free phthalocyanines were obtained from the corresponding phthalonitrile derivatives. All compounds were characterized by using mass, 1 H , 19 F NMR, UV-vis and FT-IR as well as elemental analysis. Tetra substituted Zn ( II ) phthalocyanines are slightly soluble only in THF (Compound 4a and 7a are insoluble) but metal free phthalocyanines are not soluble. Octa substituted Zn ( II ) and metal free phthalocyanine are soluble in polar solvents such as THF and DMSO.

scholarly journals Water promoted allylic nucleophilic substitution reactions of (E)-1,3 diphenylallyl acetate

2018 ◽  
Vol 20 (2) ◽  
pp. 425-430 ◽  
Author(s):  
Seema A. Ghorpade ◽  
Dinesh N. Sawant ◽  
Arwa Makki ◽  
Nagaiyan Sekar ◽  
Jörg Eppinger
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Allylic Alkylation ◽  
Substitution Reactions ◽  
Allylic Amination ◽  
Metal Free ◽  
Nucleophilic Substitution Reactions ◽  
Water Based

A transition metal free, reagent free, only water based, greener protocol for the allylic alkylation, allylic amination, and O-allylation of (E)-1,3-diphenylallyl acetate is described.

Visible-light-induced dual C–C bond formation via selective C(sp3)–H bond cleavage: efficient access to alkylated oxindoles from activated alkenes and simple ethers under metal-free conditions

2017 ◽  
Vol 19 (7) ◽  
pp. 1732-1739 ◽  
Author(s):  
Dong Xia ◽  
Yang Li ◽  
Tao Miao ◽  
Pinhua Li ◽  
Lei Wang
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Metal Free ◽  
Efficient Access ◽  
Oxidative Difunctionalization

A visible-light-induced oxidative difunctionalization of activated alkenes with simple ethersviaselective C(sp3)–H bond cleavage and dual C–C bond formation was developed.

A base-catalyzed cycloisomerization of 5-cyano-pentyne derivatives: an efficient synthesis of 3-cyano-4,5-dihydro-1H-pyrroles

2014 ◽  
Vol 50 (83) ◽  
pp. 12490-12492 ◽  
Author(s):  
Jia Meng ◽  
Yi-Jin Li ◽  
Yu-Long Zhao ◽  
Xiu-Bin Bu ◽  
Qun Liu
Keyword(s):  
Terminal Alkyne ◽  
Efficient Synthesis ◽  
Metal Free ◽  
Efficient Access

A base-catalyzed cycloisomerization of 5-cyano-pentyne bearing a terminal alkyne group has been developed under metal-free conditions. This reaction provides an efficient access to 3-cyano-4,5-dihydro-1H-pyrroles with 1,3-cyano migration as the key transformation.

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