Aerobic Transition-Metal-Free Synthesis of 2,3-Diarylindoles and 5-Aryluracils via Oxidative Nucleophilic Substitution of Hydrogen Pathway

2015 ◽  
Vol 37 (1) ◽  
pp. 112-115 ◽  
Author(s):  
Jin Yu ◽  
Hye Ran Moon ◽  
Su Yeon Kim ◽  
Jae Nyoung Kim
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Metal Free

scholarly journals Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

2018 ◽  
Vol 14 ◽  
pp. 2618-2626 ◽  
Author(s):  
Lidia A Smyshliaeva ◽  
Mikhail V Varaksin ◽  
Pavel A Slepukhin ◽  
Oleg N Chupakhin ◽  
Valery N Charushin
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Advanced Materials ◽  
Synthetic Approach ◽  
Nucleophilic Substitution Of Hydrogen ◽  
One Pot ◽  
Metal Free

The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (SN H) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials.

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.

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.

Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride

2018 ◽  
Vol 16 (41) ◽  
pp. 7564-7567 ◽  
Author(s):  
Yibiao Li ◽  
Shuo Huang ◽  
Chunshu Liao ◽  
Yan Shao ◽  
Lu Chen
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Efficient Method ◽  
Free Access ◽  
Metal Free ◽  
Catalyst Free ◽  
Hydrolysis Of

Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed.

Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP

2015 ◽  
Vol 13 (13) ◽  
pp. 3982-3987 ◽  
Author(s):  
Jie Zhang ◽  
Ying Shao ◽  
Yaxiong Wang ◽  
Huihuang Li ◽  
Dongmei Xu ◽  
...  
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Amino Acid Esters ◽  
Dimethyl Malonate ◽  
Metal Free ◽  
New Strategy ◽  
Efficient Construction ◽  
Acid Esters

A new strategy has been developed for the synthesis of α-amino acid esters via a tandem hydrolysis/decarboxylation/nucleophilic substitution using TBAI/TBHP.

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

2019 ◽  
Vol 55 (87) ◽  
pp. 13124-13127 ◽  
Author(s):  
Zhicheng Fu ◽  
Simin Sun ◽  
Anjian Yang ◽  
Fang Sun ◽  
Jiaxi Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Free Access ◽  
Metal Free

3,4-Dihydro-1,2-oxaphosphinine 2-oxides are synthesized through tandem intermolecular nucleophilic addition and cyclization of phosphonochloridates and enones in the presence of base.

(Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

2019 ◽  
Vol 17 (31) ◽  
pp. 7315-7319 ◽  
Author(s):  
Xianglin Luo ◽  
Yibiao Li ◽  
Xiuwen Chen ◽  
Zhiyan Song ◽  
Junyi Liang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Thiyl Radical ◽  
Intramolecular Cycloaddition ◽  
Free Condition ◽  
Metal Free ◽  
Novel Method

This protocol provides a novel method for the synthesis of (Z)-tetrahydrothiophene derivatives through the formation of C–S bonds under transition-metal-free condition using thiyl radical intramolecular cycloaddition cascade strategy.

Synthesis of (benzenesulfonyl)difluoromethyl thioethers from ((difluoromethyl)sulfonyl)benzene and organothiocyanates generated in situ

2021 ◽  
Author(s):  
Cheng Wu ◽  
Xiao Shen ◽  
Jian-Jun Dai ◽  
Jun Xu ◽  
Hua-Jian Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Metal Free

Easily available aryl and alkyl thiocyanates were converted into the corresponding (benzenesulfonyl)difluoromethyl thioethers via direct nucleophilic substitution of ((difluoromethyl)-sulfonyl)benzene under transition metal free conditions. Combined with various thiocyanation methods, this...

Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines

2019 ◽  
Vol 17 (32) ◽  
pp. 7438-7441 ◽  
Author(s):  
Ju-You Lu ◽  
Bo Zhao ◽  
Yongmei Du ◽  
Jianxin Yang ◽  
Jian Lu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Metal Free

An efficient C(cage)–heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines under transition-metal-free conditions. The process utilizes readily available carboranyllithium nucleophile, and exhibits a broad substrate scope.

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